


Chauffeur

by hey_you_with_the_face



Category: Supernatural
Genre: Anal Sex, Car Sex, Character Death, Chauffeur Dean, Consensual Name Calling, Crime boss Meg, Hand Jobs, Homophobic Language, Infidelity, M/M, Making Out, Organized Crime, Plot What Plot/Porn Without Plot, Public Blow Jobs, Public Sex, Riding, Rough Sex, Strip Tease, Trophy Husband Cas, Unhappily married Cas, Violence
Language: English
Status: Completed
Published: 2016-06-29
Updated: 2016-10-15
Packaged: 2018-07-18 22:36:09
Rating: Explicit
Warnings: Major Character Death, No Archive Warnings Apply
Chapters: 7
Words: 24,274
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7333363
Author URL: https://archiveofourown.org/users/hey_you_with_the_face/pseuds/hey_you_with_the_face
Summary: <blockquote class="userstuff">
              <p>Dean gets a steamy proposition from his employer's husband late one evening...</p>
            </blockquote>





	1. Chapter 1

Taking a job as a chauffeur for a well known business woman had seemed like a very easy way to make some money all those months ago when he was jobless and very close to being homeless but Dean was quick to realize there were many downsides to his new job.

One was having to wear a full suit at all times while he was working. He understood that he needed to look well groomed and professional when he was driving his employer to her meetings and work and her and her husband to their important events but wearing a three piece suit to take her to places such as friends’ homes and to her office on the weekends or dropping her husband off at the gym or the park for his weekend weekend runs seemed a bit excessive. Dean wasn’t saying he should get to wear a t-shirt and jeans but he thought a nice pair of slacks and a polo should be sufficient for the less fancy trips. Suits were expensive and his bank account wept every time he got his dry cleaning bill.

The second thing that Dean discovered was slight damper on his job was the danger factor because, due to his desperate need for employment, he hadn’t actually done any research into his potential employer until after he had signed on; if he had done even the most basic search, Dean wouldn't currently be working for a crime boss.

It turned out that Margaret Novak, his boss, was one of the reigning crime lords in the city when she wasn’t building up her shipping empire that is. Apparently having access to her own boats, trucks and airplanes allowed her to be a huge player in the drug trade. Dean wasn’t really supposed to know this but it turns out that the partition between the front of the town car and the back wasn't as soundproof as his employer thought and, since music was forbidden when he was driving with a passenger, he heard everything whether he wanted to or not. Every time he picked up shady looking businessmen or obvious thugs, Dean wondered if he was going to overhear something that would lead to one way trip to the river in the trunk of the very car he drove every day.

All in all, Dean was able to get used to all of these obstacles over time since he was paid a decent wage and driving people around was a pretty easy job once he got used to it and silenced the little voice in his head that said he was going to end up getting killed in a hit on his boss one day but there was one thing he couldn’t stand.

Beep-beep! Beep-beep! Beep-beep!

Dean groaned as he buried his head under his pillow hoping to block out the piercing tone of his work cell. The damn thing couldn’t possibly be going off again tonight.

It felt like barely any time had passed since he had fallen into bed after getting home from a long day and evening of lugging his boss all across the city. His last run had been an unscheduled pick up of his boss from a charity event at a museum downtown. Mrs. Novak had texted him just as he was sitting down to eat an extremely late supper informing him she needed taken to the office immediately. The upside to this summons was she had told him he could take the rest of the night and tomorrow morning off.

What a crock of shit that promise had been.

Resigned to the fact that his phone was indeed announcing that he had new marching orders, Dean poked his head out from under the pillow, it was too hot out to keep it over his face anyway, and squinted bleary eyed at his alarm clock. The digital numbers flashed the ungodly hour of two A.M. at him.

“No,” he grumbled, reaching clumsily for to dreaded device on his night stand. “You can’t be fucking serious. Don’t these people ever sleep?”

Sure enough, he had a shiny new text message but surprisingly it wasn’t from his boss. The message was only a few minutes old thankfully, making the big wigs wait wouldn’t end well for him.

_From Mr. Novak: I need picked up. The art museum downtown._

_Well_ , Dean thought tiredly as he crawled out of bed, trudging over to where he had, by some stroke of luck, hung up his suit from earlier before collapsing in bed. _I suppose I can’t complain, he never made any promises about me having the night off._

He sent a quick text confirming that he was on his way, and also apologizing for his delayed response just to be safe before donning his slightly wrinkled suit. He had planned on going to the dry cleaner’s this morning since he was out of clean suits so he hoped this one would do for tonight; besides it was a last minute thing and his employer’s husband won’t even notice. No one notices the chauffuer, not really.

 

Twenty minutes later found Dean pulling up to the curb in front of the same museum that he’d picked up Mrs. Novak several hours earlier to find Mr. Novak standing by the steps, holding his tuxedo jacket over his shoulder and looking decidedly unhappy.

This was not a good sign.

Lately Dean had noticed that Mrs. Novak was having problems with her hubby and that most of the fights centered around how much she was working. About a month ago on the way home from an event for orphaned children, endangered animals or whatever cause his boss had decided to endorse that night in order to keep a squeaky clean public image, they had had a very heated argument in the backseat for which, of course, Dean was a front seat witness.

“I don’t understand why you’re getting so upset about this Castiel,” Mrs. Novak’s clear business like tone had come filtering through the privacy partition. She sounded annoyed but that condescending kind of annoyed, like someone who was quickly getting tired of a small yipping dog. “I stayed at the damn party so you wouldn’t be left to fend for yourself instead of going to meet with Azazel despite the fact that we had important business matters to discuss.”

Mr. Novak had picked up on Mrs. Novak’s attitude, obviously, and was not pleased. “I’m ‘upset’,” he replied peevishly, putting a sarcastic emphasis on the word upset, “Because you dragged me to this event because it would be good for your image and then spent over half of it on your phone, leaving me to deal with all the people who wanted to talk to you since you were too busy.”

“Oh, like you didn’t enjoy getting to play hostess,” Mrs. Novak tossed back bitingly and the conversation deteriorated from there. Dean could practically feel the resentment emanating from the rear of the car, not that he could blame the other man; Mrs. Novak liked to use any chance she had to emasculate her husband. Luckily for Dean however, they reached the house soon after and they exited the car without waiting for him to open the door, arguing as they went.

All in all, Dean couldn’t decide if listening to his employer’s marital problem was better or worse than listening to an alarmingly large and tattooed man calmly discuss where he should dump a body with Mrs. Novak and the other various “business” related matters he overheard while driving.

 

Getting out of the car, Dean rounded the hood so he could open the door for Mr. Novak. The man nodded in greeting and entered the car without another word. Dean shrugged off the strange lack of greeting, Mr. Novak usually at least said hello to him but he supposed that the other man didn’t look like he was in a very good mood so he got back into the car and started to drive back to the Novak’s home.They had only made it a block away from the museum when something unprecedented happened.

Mr. Novak rolled down the privacy partition.

Dean was at a complete loss at what to do. During all the months that he had been driving for Mrs. Novak, not one time either Mrs. Novak or Mr. Novak actually opened the window that separated the back of the car from the front; if they needed to talk to him, either to change the destination or to give him further instructions, they used the intercom feature. The only time Dean saw either of them or the other passengers was when he opened and closed the rear doors.

“Uh..Y-yes Mr. Novak, is there anything wrong?” Dean stammered, trying to sound like a professional but not quite knowing what to say or expect from this turn of events.

In the rearview mirror Dean saw Mr. Novak lounging in the backseat, a strangely thoughtful look on his dark features. Usually the dark haired man had a pleasant expression on his handsome face, at least when his wife wasn’t around, so it was odd to see him wearing a calculating expression that was eerily reminiscent of Mrs. Novak.

“Well I suppose that answer depends on what you mean by wrong,” Mr. Novak replied, his tone was tired and somewhat bitter and his voice was even more gravelly than normal. He leaned forward so Dean could see him better and his eyes met Dean’s in the reflection of the rearview mirror; his eyes were an intense shade of blue, something Dean had never really noticed before. “If you mean is there something wrong in regards to the ride home? No, there’s nothing wrong. If you mean is there something wrong with my life? Then yes, there are some major problems.”

Oh no, this could not be leading anywhere good. Why was his boss's husband posing such personal questions to him of all people? And what was he even supposed to say to that?

“Um, well, I’m glad to hear that there’s nothing wrong with my driving sir,” Dean said, laughing a bit nervously. He hoped that going for humor and trying to ignore the second half of the previous statement would get him out of the potential minefield he was in.

This ploy appeared to have actually worked; the partition stayed down but there was silence from the back so Dean assumed that he was safe. He was still a bit unnerved and felt strangely exposed due to the open window behind him but all he had to do was endure this for a while longer and then he could go home and sleep. Just as he was daydreaming about his cozy bed, imagining how comfortable it was despite the heat of his apartment, Mr. Novak spoke again.

“I never actually wanted to marry her you know,” he said calmly.

Dean almost crashed into a pricey looking BMW that was stopped at the light in front of him, his hands gripping the steering wheel tightly. Why was this happening to him? Why was his boss's husband drawing him into their marriage issues? There was no way that this was going to end well for him, no way in hell.

Being met with Dean’s silence, Mr. Novak continued speaking. “The only reason I married Meg in the first place was to make my father happy, the fact that she’s richer than God helped a little too,” the man in the back mused almost idly, a barely there smile touching his lips. Dean could see that he was toying with his gold wedding band, staring at it intently. “I thought that being a trophy husband would be easy, go to fancy parties, help Meg schmooze potential business partners, help keep up pretenses but I was wrong. I can’t stand it; she thinks she can just run out and leave me to deal with her damned galas all the time. I’m getting sick of getting abandoned at these things.”

He looked up to catch Dean’s eyes in the mirror, obviously expecting some sort of response to this little story. Deann stared back as much as he could while driving and frantically tried to find something, anything, to say.

“Well sir,” Dean said slowly, pleading silently to any deity that might be listening that this would satisfy Mr. Novak and get him out of this situation, “It’s not really my place to say but maybe this is just a rough patch. Maybe in a couple weeks you and Mrs. Novak will kiss and makeup and everything will be fine.”

To his shock, Mr. Novak laughed a full on belly laugh at this, slapping his thigh lightly in amusement. This went on for several minutes before he sighed and looked at Dean with a smile.

“Oh Dean,” he said, slightly breathless after all that laughing, “Thank you for that, I really needed a good laugh.”

_Shit, oh shit_ Dean thought to himself as his stomach roiled in anxiety, _what the hell did I do? I should’ve kept my mouth shut._

It was obvious that he wasn’t getting out of this without either losing his job at best or losing some dearly loved appendage at the worst so he decided to make what happened to him worth it.

“Did I say something amusing sir?” Dean asked, making his tone as neutral as possible to avoid accusations of sarcasm. Mr. Novak chuckled, a deep warm sound that filled the car.

“That bit about kissing and making up,” Mr. Novak replied, wiping at the tears of laughter in his eyes, “It’s a lovely idea Dean but we really aren’t the type of couple to do that.”

Unable to quell his curiosity now that he had thrown himself off the deep end, Dean stupidly asked, “Why not sir?”

Mr. Novak met Dean’s gaze in the rearview mirror again. “Because Meg isn’t exactly my type,” he said, looking at him pointedly before continuing, “Oh and Dean, enough of this sir business; you can call me Cas.”

And with that one statement, coupled with the now slightly heated gaze he now saw in the rearview mirror, caused Dean’s brain to short circuit as he put the puzzle pieces together.

_Oh._

If Dean had thought he’d been surprised earlier when Mr. Novak had started this impromptu marriage counseling session, having his boss's husband practically declare that he was gay and that his marriage was a sham threw him completely for a loop. Luckily they were currently driving down one of the more deserted stretches of road because this time he most definitely would have crashed into another car if one had been present since his mind was sorting through all of the interactions he’d ever had with Mr. Novak in the past.

“It would appear that I’ve shocked you,” Mr. Novak said. He sounded very pleased with himself. “But that’s to be expected, I’m very good at blending in and keeping my personal preferences private. It was one of the reasons I was told to marry Meg. You see she didn’t want to get married but her father was looking for someone to marry her off to and my father was very keen on getting a hold on her family’s money. Meg agreed to marry me because she knew from the minute she saw me that I had no real interest in her so she could do what she pleased and keep her father happy; everyone got what they wanted, or at least almost everyone.”

There was a very distinct tone of bitterness in Mr. Novak’s voice that piqued Dean’s already highly dangerous levels of curiosity. “What do you mean sir, I mean Cas,” he amended quickly at the look from the man in the backseat, “About almost everyone?”

Mr. Novak, Cas, he mentally corrected himself, smiled at him. His handsome smile was practically dripping with disdain and it bled over into his voice as he explained. “What I meant was, when we first got married Meg and I had a deal; we could do as we please in regards to sexual partners as long as we were discreet and that worked fine. That is it worked fine until she got into the public eye and decided that is was far too risky for me to meet other men. What would happen if I were found out and someone tried to use this against her?”

Dean winced sympathetically; he knew how that felt. His father had always encouraged him to keep his preferences quiet, said that this would make it easier on him to get a job. Personally he found that it didn’t matter either way considering most people wouldn’t even call him in for an interview because he “didn’t possess the skills or experience they were looking for.” The only reason he had gotten this job was because Mrs. Novak wanted someone pretty to drive her pretty car around, a matching set, and lucky for him, the one thing he did possess was classic good looks. Tall with short brown hair and green eyes, Dean knew that he filled this requirement quite well.

“That was about five years ago,” Cas continued, once again leveling a speculative look at him, “Five years of forced celibacy Dean, all because she’s afraid I might get caught. I was forced to put up with it of course; she has her cronies keep tabs on me, making sure I behave myself. There didn’t seem to be a way around it but now that you’re here, that can change.”

Dean blinked in shock, he peered questioningly over his shoulder before looking back at the dark expanse of road. “What do I have to do with anything?” he asked in confusion before catching on, “Oh, you want me to drive you to meet men and for me to keep quiet about it. I suppose that since you’re my boss to I would have to do as you say.”

Once again, Cas chuckled; Dean’s stomach tightened slightly, that laugh had not been the precursor to good things so far and he braced himself for what might come next.

“Very creative solution Dean,” Cas said with a smile but then he shook his head, “But no, I’m afraid that wouldn’t work as Meg is very good keeping her eyes on me. The solution to my problem is much simpler, I want you to be my lover.”

This time Dean hit the brakes in his shock over this blunt confession and the car lurched slightly before resuming its course. Tearing his eyes from the road, he stared in disbelief at the man he was chauffeuring; the other man’s expression was calm but with a slightly smug air to it but other than that, totally sincere. The man was serious.

This couldn’t be happening. His boss's husband did not just proposition him for sex after telling him about his sham marriage. This shit did not happen in real life. He had to be going insane; that was the only logical solution. Maybe he was still at home in bed and he was dreaming; that was way more possible than this.

Cas’ voice started him out of his thoughts.

“I’m waiting for an answer,” he said in a voice that, in Dean’s opinion, was way too level for a situation like this. “I wouldn’t force you into this, I’m not that sort of a man but I’ve noticed the way you look at me sometimes. I can tell that you want me.”

He wasn’t exactly wrong there. Dean had noticed how attractive Cas was. The man could wear the hell out of an Armani suit but he also looked devastatingly hot when he picked the man up after his weekend runs, dressed in loose fitting workout clothes and dripping with sweat. So Dean had taken a peek here and there but it hadn’t been more than that. Until ten minutes ago, he’d thought the man was straight for crying out loud.

“I-I’m just not sure if that would be appropriate, Cas, I mean sir,” Dean scrambled to say, not that there was anyway to salvage this. If he said no, the man would probably see that he was fired in order to protect his secret. The other option would be to say yes, because sleeping with Cas would not be a hardship in anyway, but that would mean he risked pissing off his extremely powerful, well connected and violent boss.

“You wouldn’t have to worry about Meg,” Cas said soothingly, reading Dean’s mind, as he leaned forward so he could speak through the window. “She thinks that you’re straight and quite honestly she doesn’t really see the help as actual people so she wouldn’t suspect a thing.”

Dean worried his lower lip between his teeth. He was crazy, he had to be if he was actually considering this for even a second but Cas was a very hard man to resist. That deep rough voice, those darkly handsome features and an actual offer for sex coupled with Dean’s pre-existing attraction to the man was drawing him in despite the fact that it would be a total disaster. He was just about to try and reason with Cas that it would not be a good idea to risk Meg’s wrath when a rustle of fabric interrupted his thoughts. Glancing up at the mirror, Dean inhaled sharply at what he saw in the back seat.

Cas was stripping out of his tuxedo.

He watched as Cas finished untying his bowtie before pulling on the fabric so it slithered to the floor. Next his fingers deftly removed his cufflinks so the sleeves of the dress shirt hung loosely around those elegant hands and wrists. Dean was transfixed, the speed of the car slowed to a crawl as his foot let off of the gas pedal, and he could do nothing but gape in shock.

Cas began to slowly undo the buttons of his shirt, his eyes locked on Dean’s through the mirror and a knowing smile on his lips; the heat in those eyes sent a tingling sensation down his spine and, despite being how warm he’d been in his suit mere seconds before, Dean shivered. His breathing sped up minutely as the shirt parted to reveal tan skin and chiseled muscles, the muscles he had gotten glimpses of in the past when driving the other man to and from the park he ran at on weekends; he’d be lying if he said he’d never fantasized about what Cas would look like shirtless, he didn’t do it often but it had happened. His fantasies had nothing on the real thing.

The shirt fell to the seat leaving Cas bare chested; the other man ran his hands lazily over his skin, stopping to tease his nipples then traveling further down to toy with the dark hair trailing down into his dress slacks. Looking up at Dean, he raised an eyebrow and smiled impishly before he leaned back on the seat, his legs spread wide. The dark material of the slacks was pulled taut against against the obvious erection there. Dean swallowed heavily and felt his cock twitch in his pants; he tightened his hands on the steering wheel, fighting the urge to turn around and touch that perfect body or at least touch himself.

Just as Dean thought things couldn’t get worse, or better depending on the point of view, Cas stopped palming the bulge in his pants and reached for the zipper before pulling it down teasingly slow; the other man sighed happily as he reached a hand into his pants and freed himself. From what Dean could make out in the rearview mirror, his cock was flushed and almost fully hard. Dean ached; he wanted to be the one back there holding that thick cock, stroking it slowly and feeling the heat and weight of it in his palm. Then Cas began thrusting his hips up languidly into his hand, coupling the movement with lazy strokes; Dean felt like his own dick was going to burst through the delicate zipper on his slacks and that his head was going to explode. He had no idea how he was supposed to control himself.

“Pull the car over Dean,” Cas ordered from the back of the car, his breathing was starting to get heavy. He was still tugging on his length and eyeing Dean like a predator waiting to strike. “You don’t have to join me if you don’t want to but I am going to get myself off right here in this car whether you help me or not, your choice.”

Dean shuddered as a wave of heat washed over him and made its way to settle in his groin. He did want, he wanted very badly to help Cas. The man was gorgeous and spread out on display like any one of Dean’s wettest dreams and his hands tingled with the need to find out if that body was as hard and firm as it looked. Unfortunately there was also the threat of Cas’ wife to factor into things but it was getting harder and harder to remember why he was worried the longer he listened to the sound of Cas’ heavy breathing coupled with the occasional low gasp of pleasure.

Following his new orders, Dean found a place to pull over. There was a roadside diner just up the road and at this time of night, the parking lot was empty. He parked the car in the back corner of the lot, far from the road, and turned off the car. Now that the sound of the engine was gone, the sounds of Cas pleasuring himself echoed loudly in his ears. Dean clenched his hands on his thighs, trying valiantly to quell his lust and ignore his throbbing cock, trapped almost painfully in his pants.

“Oh Dean,” Cas moaned, the slick sounds of flesh on flesh filling the car, “Oh fuck!”

That was the straw that broke the camel’s back and Dean snapped. There was only so much he could resist and the sound of the man in the back seat calling out his name while he fucked into his own fist was just too much.

He fumbled out of his seat belt and practically leapt out of his door so he could rip open the back driver’s side door, revealing a flushed but smug looking Cas; he was still stroking himself but he stop as the sight of Dean’s wild entrance.

“Are going to just stand there,” Cas said teasingly, patting the seat beside him invitingly, “Or are you going have a little fun with me?”

Dean nodded eagerly as he quickly stripped off his suit jacket and, after some fumbling, his waistcoat and shirt; goosebumps erupted on his arms as his hot skin was exposed to the cool air. Cas’ eyes took in the sight of his naked chest hungrily and he patted his thighs; Dean maneuvered himself so he was straddling the other man, hissing as this put pressure on his cock in his unopened slacks.

Cas chuckled at his predicament but took pity on him and unzipped his pants; the chauffeur groaned in relief, a groan that turned into a gasp as a hand slipped into his underwear to cup his aching erection.

“Let’s get these pants off shall we?” the other man suggested, pushing slightly at the waistband of Dean’s dress pants. Dean did as he was told and reluctantly removed himself from Cas’ lap so he could peel off his slacks and underwear; his boxer briefs were already sporting a damp spot in the front. By the time he was completely naked, Cas had removed his own clothes and Dean took a second to drink in the sight. All that exercise had obviously paid off, the man was well muscled and lean; his eyes trailed from faintly defined abs and down the subtle vee of his hips to rest on dark thatch of hair surrounding Cas’ hard cock.

Wasting no time, Dean reclaimed his place in Cas’ lap, both men gasped as their dicks rubbed together slightly. Cas reached up to grasp at the hair on the back of Dean’s head and used it to yank him down into a heated kiss, thrusting his tongue into the chauffeur's mouth, claiming him. Dean moaned into the kiss, rocking his hips gently and wrapping his arms around the shoulders of the man beneath him.

Cas broker the kiss so he could plant kisses down the side of Dean’s shoulder and settling to suck a mark onto his collar bone but once he’d moved away and Dean tried to return the favor, Cas stopped him with a hand over his lips.

“Sorry sweetheart,” he said panting, “No marking for you, we have to be discreet.”

A little disappointed, Dean contented himself with attacking the other man’s mouth again, pouring all his frustrated desire into ravaging Cas’ mouth. They made out frantically for the next couple minutes, hands wandering over each other, discovering what made each other shudder and gasp and moan. Eventually Cas ran a hand down to brush their leaking cocks; Dean’s hips bucked up into the contact. He was so hard that it was starting to hurt. Wrapping a hand around their neglected cocks, Cas started to stroke them in tandem. His pace was painfully slow and a disappointed whine escaped Dean before he could stop it.

This sound caused Cas to chuckle but he got the message clearly and decided to take pity on them both; he gripped them tightly together and sped up his hand. The friction was fantastic and caused sparks of pleasure to flash up and down Dean’s spine. He braced his knees on the seat and gripped onto Cas’ shoulders and began moving sinuously in the other man’s lap, fucking his hips up into the channel Cas had created for them. The man beneath him groaned as this added to the sensations.

“God, Dean,” Cas gasped, starting to add the occasional twist to the end of his strokes, “You have no idea how good you look, writhing on my lap like this.” Dean whimpered in acknowledgement, his hips never stopping their stuttering thrusts upwards. “Someday I’m going to fuck you in this car, just like this. You, bouncing in my lap while I pound into that needy hole of yours. I bet you would come so hard for me, harder than you are going to come for me right now.”

Dean’s stomach started to tighten, he was so close now. Cas had to be close too, he was starting to thrust up into his fist as well and his strokes were getting tighter and faster. They writhed together, chasing their orgasms. The windows of the car were fogging up due to their combined heat and they were sweating, the sweat making their skin slick and easing their movements. The image that Cas had painted pushed Dean closer and closer making him move his hips faster and faster; he couldn’t stop, he needed to come.

Cas suddenly froze, crying out Dean’s name as he came. The splash of warmth on his own cock and stomach had Dean falling over the edge with a shout, hips grinding up into Cas’ fist as the other man worked them through their orgasms; he eventually released their spent cocks as they grew sensitive. Dean collapsed over Cas, laying his head on the other man’s shoulder. They sat in silence while they came down; the sound of their panting breaths were the only sounds in the car as the sweat cooled on their bodies and their heartbeats slowed.

Eventually the cooling mess on their stomachs prompted them to move, wiping themselves clean with some tissues from a container that was kept in the back of the car. There was an awkward tinge to the air as they pulled on their clothes and this was enough proof for Dean to know that he’d screwed up royally.

Bracing himself for his inevitable firing, he turned to look at Cas. The other man looked as if nothing were amiss, like it was completely normal for a man to exchange handjobs with his wife’s chauffeur in a darkened parking lot. He opened his mouth to say...something, anything, when Cas stopped him.

“You’re probably freaking out, wondering if we’d just made a mistake,” Cas said, reading his mind once again. Dean nodded reluctantly in confirmation. The other man sighed tiredly as he pulled on his shirt. “I thought so, I want you to know Dean, Meg cares so little for me and notices so little of you that there is no way we’ll be found out. As long as we’re available when she calls, she will never notice anything is amiss. But, if you truly don’t want to risk it, I won’t force you to do this again.”

Dean thought critically for moment. On one hand he should stop this in its tracks before he ended up chopped up into little pieces and scattered fed to hungry dogs but on the other hand, he’d already crossed the line, the crime had been committed. He was screwed either way now, he might as well enjoy himself for as long as he could. Besides, he felt bad for Cas, the man was just looking for a bit of companionship. Decision made, for better or worse, he pulled Cas in for a lingering kiss before breaking away and grinning devilishly.

“Where to next sir?” he asked playfully. Cas burst into a wide grin.

Maybe there were a few upsides to this job.


	2. Chapter 2

“Why is this damn art festival so damn important Castiel?”

Dean stood stoically by the open car door as his employer and her husband marched down the walkway of their home, more like mansion, and kept his gaze strategically on a shrub in his eyeline. This helped him to look uninterested in not only his passengers but their heated conversation despite the fact that he was actually extremely interested in both.

“It’s important because it’s literally the one thing I get to do every year that is totally and completely about me,” Cas shot back irritably as they finally arrived at the doors. Meg, as Dean had started to refer to her in his head since that was what Cas always called her, rolled her eyes as Dean reached out a polite hand to help her negotiate her way into the car with a muttered ‘ma’am.’

He turned back once his employer was settled to see Cas waiting to enter the car. The other man’s face was slightly flushed, most likely from anger if the current debate was anything to go by, and he looked approximately one step away from screaming in frustration; the sight bothered Dean enough that he brushed hands with Cas accidentally on purpose while moving to let him into the car and flashed him a discreet smile. Considering how potentially dangerous it was to show any type of affection to his boss’ husband, he wasn’t surprised when Cas’ stormy expression didn’t change but Dean fancied that he saw those icy eyes thaw for a brief second in acknowledgement.

“Thank you, Dean,” Cas said politely, if a bit more curt than he usually did, when Dean opened the car door for him. The chauffeur caught a glimpse of him turning sharply towards his wife and a quick burst of angry voices right before he shut the door. Taking a deep breath, Dean walked briskly around to the driver’s side of the car and got in; he turned on the car and started the drive to the building Mrs. Novak’s offices were located.

Not surprisingly, he had a soundtrack to the drive courtesy of his passengers.

“You dictate every single aspect of my life Meg, I just want one day where I can go and enjoy myself now you want to deny me that because you don’t have someone to be my shadow,” Cas’ voice sounded loud and clear through the closed partition.

Dean heard the distinct sound of Meg scoffing at Cas’ argument. “You are such a pain in my ass,” she said irritably, “I told you, I have a very important meeting with a new business partner and I need all my security detail there. I’m sorry that that means you have to miss your little trip but you’re just going to have to suck it up and deal with it.”

There was an extremely long silence. It was long enough that Dean was actually starting to worry that Cas had finally snapped and killed the bitch. He was seriously considering “accidentally” hitting the partition button just to get a glimpse of what was going on when the intercom flared to life and the sharp tones of Mrs. Novak issued forth.

_“Winchester.”_

“Yes Mrs. Novak?” Dean said, trying to act like he hadn’t been eavesdropping and thinking she had been bludgeoned to death by her furious husband.

_“Cancel your plans for this weekend. I need you to drive and accompany Mr. Novak on a weekend trip. You will pick him up at the house Saturday morning and drop him off Sunday night, you will be compensated for your time.”_

“Of course, ma’am,” he replied quickly, not wanting to piss her off any further. The intercom fell silent and Dean shook his head slightly.

Okay, that was unexpected.

Dean spent the rest of the day wondering just what the hell had happened in that ten minutes of silence that caused his boss to actually compromise. He had seen some of the men she dealt with and they always came in second to Meg’s iron will and made a mental note to ask Cas.

 

The rest of Dean’s week went along as usual, getting up early to drive people around, driving people around at lunchtime, getting woken up in the middle of the night to drive people around, etc but the chauffeur didn’t really care. He was going to get to be alone with his boss’ husband/newly discovered sex partner for most of the weekend and this realization had Dean’s mind whirling with filthy scenarios.

Maybe Cas would make good on his promise to fuck him in the car.  
Maybe they’d test out the hotel’s bed.

If he was really lucky, maybe he’d get both. He’d only gotten a brief glimpse of Cas sexual side that night but one thing Dean would bet money on was that the other man would be an absolute animal in the sack. The man had five years of pent up sexual energy to work out and the chauffeur would gladly throw himself on that grenade.

Around mid-morning Saturday found Dean putting Cas’ overnight bag to join his own in the back of one of the Novak’s less flashy cars. They wouldn’t be taking the limo this weekend; Meg had had Cas inform him that she wanted the usual car left in the city on the off chance that she might need it. This hadn’t seemed to bother the other man, in fact he’d seemed especially pleased about this turn of events but wouldn’t elaborate as to why this was a good thing.

Dean settled behind the wheel once Cas’ was safely ensconced in the back seat. “Ready to go Mr. Novak?”

The man in the back seat nodded and met his eyes blearily over the rim of a travel mug. It seemed that Cas wasn’t quite awake yet this morning. “Yes, Dean,” Cas said, yawning slightly, “We’re all set I believe.”

Chuckling at the slightly grumpy look on the other man’s face, Dean turned his attention back to the front and started the car. “It’s about three hours to the hotel we’ll be staying at, you could catch a bit of a nap if you want,” he suggested as he navigated the car down the driveway and onto the street. 

“Oh no,” came the response from the back, “I plan on enjoying every second of my time from under that woman’s thumb, even the car ride. Speaking of which, pull the car over for a second Dean.”

Stifling the urge to ask why, Dean did as he was told and pulled the car into a side street and put it into park. The car had barely stopped moving before the back passenger door was opening and closing, shortly followed by the opening of the driver’s door. Dean could only look up with shock and confusion.

“What’re you doing Cas?” the chauffeur asked as the other man peered down at him.

Cas gestured in response, “Get out of the car Dean,” he said briskly. When Dean could only stare in horror, thinking that he was getting fired or maybe Cas was going to make a break for it and try to escape the ogre he was married to and leave him here to explain what happened to said ogre, he continued, “I haven’t been allowed to drive myself anywhere in years, I want to actually sit behind the wheel again if you don’t have any objections.”

Oh, well that made sense. Dean mused on how he would feel being ferried around all the time and shuddered internally as he climbed out of the car to let Cas into the driver’s seat, that sounded like an awful way to live but then again the other aspects of the other man’s life were way worse than that. Instead of sitting in the backseat, he opted to sit in the passenger seat; it would feel strange to sit in the back when a front seat was open.

“Ready?” Cas asked after fastening his seatbelt and fiddling with the mirrors. Dean buckled his own seatbelt and nodded. “Good, let’s get a move on then.”

Dean settled back, trying to think of something to talk about to fill the silence. What exactly did one talk about to their boss’ husband who also happened to be the guy that had gotten him off in the back of his boss’ limo? It wasn’t like they had much in common besides a late night handjob and that wasn’t exactly roadtrip discussion material.

But boy did Dean wanted to talk about it. Wanted to ask when he’d get a repeat performance with the possibility of a more intense follow up episode. 

He shook his head slightly to dispel the thoughts of himself and Cas sprawled out in the backseat of a car parked on a back road, going at each other like animals, and stared out the window trying to find something to say. They had moved out of the city and onto the highway; Dean was distracted by the scenery flashing by and was promptly hypnotized. The last thing he remembers before dropping off as his long week of work with little sleep caught up with him was the low rumble of Cas humming along with the quiet music on the radio.

 

Dean snorted awake and waved his hands around in confusion when he couldn’t place his surroundings. An amused chuckle filtered through his addled brain causing him to look over and see Cas laughing at him as he pulled the keys out of the ignition; it was then that Dean realized the car was sitting still.

“Rise and shine, sleepyhead,” the other man crooned teasingly, his eyes obscured by a pair of aviator shades. “Time to wake up, we’re at the hotel.”

“Did I seriously fall asleep?” Dean mumbled, rubbing his eye with on hand and massaging the kink in his neck with the other. He could have sworn he’d just taken a longer than normal blink.

Cas laughed again and began to get out of the car; Dean followed, stumbling a bit due to just waking up. “Yes, I believe you started snoring about twenty minutes into the drive,” Cas answered amiably. He unlocked the trunk so the could grab their bags; Dean attempted to carry the other man’s bag but Cas was apparently taking his whole ‘enjoying being a somewhat regular person’ thing seriously.

They started walking over to the entrance of their hotel, a fancy looking building that probably meant swanky accommodations but then, the Novaks weren’t exactly hurting for money. It was just as they were getting close to the door that the other man spoke again, his voice a bit wistful.

“It’s a shame you fell asleep, Dean,” Cas said quietly as not to be overheard by the few people going in and out of the hotel, “I had hoped to tell you exactly what I plan on doing to you in this hotel after we return from the festival tonight but I guess you’ll just have to use your imagination.”

And with that, the dark haired man left him standing by the hotel door but not before flashing him a look that was practically dripping with promise. Dean shuddered as a bolt of heat flashed down his spine and he mentally kicked himself for his nap in the car; he’d missed out on listening to Cas describing what probably would have been absolutely filthy things, which was a crime in Dean’s book.

Sighing and mentally grumbling, Dean followed the other man into the hotel.

 

This had to be, hands down, the longest day of Dean’s life

Once they had checked into the hotel, the chauffeur was shocked to find out that not only were he and Cas going to be in the same room, there was only one bed. When Dean had nervously asked how Mrs. Novak would feel about them being in the same room and sharing a bed, Cas had actually laughed. Apparently his wife had been the one to insist that they share a room, most likely so that Dean could ‘keep an eye’ on him since she was still under the mistaken impression that her chauffeur is straight but the other man did admit he may have quietly asked the concierge if there was any way to acquire a queen-sized bed instead of the two fulls they had had booked, something that was accomplished relatively quickly once a bit of cash had changed hands.

This development had had Dean’s skin tingling as his brain cycled through scenario after scenario contemplating what might happen in that plush comfortable looking bed. He’d stowed his duffle one of the arm chairs and turned to see Cas digging through his own bag by the bed. Dean had walked over, grinning slyly, and pressed himself against the other man’s back and wrapped his arms around his waist.

“So how exactly are we going to be enjoying this amazing bed?” Dean had asked softly as he slipped his hands under the hem of Cas’ shirt and toyed with the buckle on his jeans. 

He had been looking forward to stripping his boss’s husband out of his clothes all week and now that the time had arrived, he could barely contain his excitement. His hands had started to trail over the heated skin of Cas’ belly when the other man brushed his hands, and then the rest of Dean away.

“What’s wrong?” Dean had asked in confusion. He’d been positive that Cas meant for them to fuck like bunnies on this trip, had he changed his mind and decided the possible consequences outweighed the reward?

Cas had turned to face him, a peculiar look graced his features, and leaned forward to capture Dean’s mouth.

The kiss had been extremely intense, not even bothering to ease into things, and had had Dean moaning wantonly. Cas had pulled him in roughly so they were plastered together. When Dean had gasped at the feel of their groins crashing together, Cas had taken the opportunity to slide his tongue into his mouth and proceeded to completely dominate the kiss. Dean had smiled internally; they were finally getting to the good stuff.

But just as he had been getting ready to suggest they move to the bed, Cas had pulled away and walked back to his bag, leaving Dean slightly breathless, aching and confused.

Cas had pulled out a light jacket and a camera before he turned to look at Dean expectantly, “Well, let’s get moving. I want to see as much of the displays as I can before dinner time.”

All that hardcore mini-making out and groping and that bastard wanted to go see some arts and crafts?! Now?!

The expression on Dean’s face must have been enough to communicate his confusion and displeasure with this development because Cas had smirked at him.

“Oh, I see, you thought I was going to throw you down and plow you into this mattress?” Cas had said as he nodded understandingly. When Dean had nodded dumbly in reply, he’d chuckled lowly, a sound that Dean had felt like a caress down his spine. “That had been my original plan, to drag you in here and screw your pretty little brains out and I had been planning to explain that to you on the drive here but you fell asleep on me.”

Dean’s hackles had risen a little at this. “What do this teasing is some sort of bullshit punishment for falling asleep?” he’d asked hotly, angry at the nerve of the dark haired man. Just because in a technical sense Cas was his boss, that didn't mean he has the right to punish him.

“Oh no,” Cas had reassured him hurriedly which caused Dean to calm down ever so slightly, “Think of this as more of a tit for tat situation.” At Dean’s sound of confusion, he’d continued, “You see my original plan for our drive here had been to tell you all about the delightful things I planned to do to you in this hotel room and maybe find a way to work a bit of road trip fun time into our schedule but...you fell asleep, leaving me all alone with my quite frankly filthy fantasies of you and no way to distract myself. I was forced to spend the entire drive turned on and frustrated while you slept comfortably.”

Dean had absorbed this information, a sinking feeling in his stomach told him he knew where this was going and hadn’t been happy about it but a very small part of him had perked up its ears in interest.

Cas had walked slowly over to him and run a hand up his chest; Dean had shivered lightly as the other man had leaned in so he could whisper in his ear. “So considering you left me alone to stew in my own arousal, I thought it was only fair for you to experience it yourself,” he’d murmured and the nipped Dean’s ear teasingly before pulling away to pretend to straighten Dean’s shirt, intentionally brushing his hands over his sensitive nipples through the fabric. 

A smirked had curled over Cas’ mouth at the responsive gasp that had escaped Dean’s mouth. “Now we are going to go to the art festival, which I have actually been looking forward to all year by the way, and while I enjoy all the displays and demonstrations, you get to think about just what may have happened right now if you hadn’t fallen asleep and what’s going to happen when we get back here tonight.”

And as if the promise dripping off of Cas’ gravelly voice hadn’t been enough to torture him with, the other man had reached a hand down to briefly massage the slight bulge in Dean’s jeans, to which the man had responded to with a strangled moan, before disappearing out the door with a call of “come along now Dean” tossed over his shoulder.

 

Now in the present, what felt like an eternity later, they were still at the goddamn art festival!

Cas was currently oohing and aahing over a sculptor’s booth and asking question after question about how the young lady came up with her subject matter. Dean was standing at the corner of the stall, trying to not look impatient but silently willing the other man to move on to the next stall. By his count, there were only about a half dozen stall left in this row which also happened to be the last row in the festival. Only six display tables of art stood between him and finally, finally getting some action.

Words could not express how frustrated Dean was at this point. When Cas had first told him about his payback scheme for ‘abandoning him to horniness’ on the drive to the festival, Dean had stupidly thought that the other man’s master plan would fail; navigating the display area of the art festival would be a distraction from his naughty thought because, even though art wasn’t exactly one of Dean’s hobbies, looking at paintings, sculptures and other pieces of art would probably keep him occupied until they went back to the hotel room. All in all, this would be a piece of cake.

Oh how foolish his several-hours-younger self had been.

One of the factors he hadn’t taken into account was the fact that trying to not thinking about sex with Cas was essentially like being told to absolutely positively not think about a pink elephant which is to say that it’s impossible. 

Images of what Cas had looked like, sweaty and debauched, stroking their hard cocks in tandem in the back of the darkened limousine kept flashing through his mind despite his best efforts to suppress them and when he was able to get rid of those mental pictures, his brain helpfully provided hypothetical scenarios taking place in the back of the car where he was on his knees, looking up at the dark haired man as he stroked himself and ordered Dean to suck him off. He was able to briefly able to shake these thoughts away only for the cycle to begin anew.

In summary, Dean’s brain was betraying him hardcore.

Not to mention the little fact of Cas’ teasing. The other man never wasted an opportunity to brush Dean’s body lightly with his hands, always apologizing as if it were an accident but the mischievous smirk on his face each time said otherwise. Other times Cas would ‘accidentally’ run into him from behind and then apologize for not looking where he was going by standing far closer to Dean than was socially acceptable and murmuring in his ear. Sufficed to say, Dean was slowly losing his mind but he could see an end to the tunnel. Only one more display left; he was practically giddy.

He was actually absorbed in looking at some pretty neat little carved animals, there was a stone dinosaur of all things, when he felt warmth at his back; rolling his eyes, he braced himself for another tease disguised as an apology but the words he’d come to know so very well over the past hours wandering the art tables didn’t come.

“I think we’re finally out of art to see,” Cas’ voice rumbled in his ear. Dean felt a hand slide surreptitiously to his waist as his hopes began to perk up, the torture was almost over. “And I think it’s time to head back to our room.”

Dean fought the urge to shout for joy and throw his arms in the air instead he chose to adopt a laid-back and, hopefully, suave demeanor. “Sounds good to me,” he replied as he pushed ass ever so slightly back into Cas’ crotch and smirked at the barely there gasp this motion earned him, “Lead the way sir.”

Cas spun him around and Dean saw there was a bit of a feral gleam in his eyes before the other man had a firm grip on his hand and was pulling him in the direction of the exit.

Interesting, he thought to himself as he was navigated down the street to their hotel, the festival was only a few blocks away from they were staying, Note to self: Cas likes a bit of power play. Not that Dean minded this in the slightest, he liked the idea of this normally calm and reserved man breaking out of his usual facade and dominating the hell out of him.

In no time at all they were finally back in the room. The fact that they didn’t burst through the door attached at the mouth was not due to any lack of effort on Dean’s part but he did have to agree with Cas argument that a little discretion was needed though the other man did risk copping a feel in the elevator during the hustle and bustle of people getting in and out, at least he hoped it was Cas.

Now that they were in the room Dean could see clear signs that the other man was losing the battle with his impatience.

“Clothes off,” Cas ordered as soon as the door clicked shut and he began to unbutton his own shirt and for obvious reasons, Dean wasn’t going to argue with this.

He quickly stripped off the t-shirt he had been wearing and noted the fact that he could practically feel Cas’ eyes traversing his exposed torso. Not one to miss an opportunity when one is presented, Dean deliberately slowed down his movements, making sure to meet those hungry blue eyes as he slowly lowered his zipper and unbuttoned his jeans. Then to make things even more interesting, he turned around and began to ever slowly slide his pants and boxers off, smirking over his shoulder where Cas had stopped all movements to take off his own clothes and was staring transfixed at the little impromptu show Dean was putting on.

Just as the denim slipped below the curve of his ass, Dean suddenly felt a presence at his back a split second before he was spun around and before he could open his mouth to say anything, Cas was on him.

“Such--a goddamn--tease!” the other man managed to growl out lowly between dominating Dean’s mouth with kisses, pausing every now and then to nip sharply at his lips. After the initial shock, Dean threw himself into the kiss, giving just as good as he got. 

Cas’ hands slid down to rest just above the top of Dean’s jeans, massaging his ass and pulling them flush together. Dean gasped as his exposed cock brushed against the rough material of the other man’s pants and he retaliated by worming a hand between them and cupping the impressive bulge he found there; he grinned in satisfaction at the surprised grunt that echoed in the quiet room as he squeezed slightly.

They made out for a few seconds more before Cas broke away. “Get on the bed,” demanded the dark haired man as he pushed at the jeans resting on Dean’s hips so they pooled at his feet before getting back to taking off his own clothes.

Dean turned to comply but paused as he saw the other man’s hands moving to undo his pants. “Wait,” he said, he grabbed Cas by the belt buckle and nudged him towards the bed, “There’s been something I’ve been wanting to do.”

Confusion was etched on Cas’ face as Dean arranged him so he was sitting on the edge of the bed but it was replaced by understanding quickly followed lust as Dean settled on his knees between his spread legs. He reached up and unbuckled the other man’s belt and eased the zipper down, all the while looking up at Cas’ face which was practically burning with want.

“I’ve been wanting to do this since that night in the car,” Dean murmured as he carefully slipped a hand into Cas’ underwear to free the other man’s hard on; Cas inhaled sharply when Dean gripped him and started stroking him slowly. “Thought about it the whole time we were at that festival.”

Cas hummed thoughtfully, reaching a hand down to cup Dean’s chin; his thumb brushed over the curve of his lip, “Well then, what are you waiting for? Get to work.”

And with a playful ‘yes sir’ that caused a noticeable hitch in the dark haired man’s breathing, Dean guided the tip of Cas’ cock into his mouth. 

The noises Cas let loose while Dean blew him at a tortuously slow pace were much hotter than anything Dean had encountered before. All the gasps, low groans and growls got his motor revving so intensely that, in the back of his mind, he was extremely happy he wasn’t wearing his jeans and underwear anymore especially considering that the view was even more attractive. He was so hard he ached but Dean didn’t bother touching himself, he knew Cas would take care of him. 

Dean looked up and took in the sight of Cas with his head thrown back in pleasure greedily before focusing back on the matter at hand, namely trying to deepthroat Cas’ thick cock. He gripped the other man’s hips tightly to keep in in place as he attempted to take him deeper. As he had been expecting, Cas jerked his hips up unconsciously.

“Dean!” he gasped as his hand tangled in Dean’s hair and tugged slightly causing Dean to moan. “Fuck, I knew you had a filthy mouth but just look at you, you’re desperate to choke on my cock aren’t you?” When Dean moaned in response he groaned. “As much as I’d like to take you up on the offer to fuck your pretty little mouth until I come down your throat,” Cas said in response to the sound of protest that escaped Dean as he was pulled off, “I would very much like to pound that gorgeous ass into the mattress.”

That was all the encouragement Dean needed to begin scrambling on to the bed; he settled on his hands and knees in the middle of the bed and arched his back, knowing it put his ass on display. There was a rustling noise he figured had to be Cas digging through his bag for what they needed but soon he felt the bed dip and, shortly after that, the other man’s hot hands brushing over the skin of his ass. Dean shivered in anticipation at the brush of fingers down to tease at his hole.

“Come on Cas,” Dean urged, nudging his ass backwards into Cas’ hands and hoped the other man would get the hint and stop with his damn teasing already. Cas laughed, obviously getting the message and got to work getting him ready; Dean groaned into the comforter, relieved that he was finally getting what he’d wanted for so long, what he’d been fantasizing about for hours at that damned craft show.

“That’s it Dean,” Cas crooned as his talented fingers thrust in and out of Dean’s hole, the action pulling more moans and gasps from Dean as he writhed on the bed, “Make those pretty noises for me.” He leaned forward, kissing his way up to whisper in Dean’s ear, “God, you turn me on so much; I just want to hold you down and fuck you until the only sound you can make is my name, over and over.”

Dean mumbled into the comforter; when Cas leaned back and asked him to repeat himself, he turned his head to look at the debauched man behind him and groaned, “Do it. Do it, Cas, please.”

There was an unpleasant moment as Cas slipped his fingers free to slide a condom on himself, leaving Dean empty but luckily he barely had time to register the feeling before the tip of Cas’ cock was nudging at his entrance. Dean’s mouth opened in a silent gasp as the other man slowly filled him up; it felt so good and ten times better than he’d imagined. Cas stilled once he’d bottomed out, giving each of them a moment; Dean couldn’t see him but he imagined that handsome face slack-jawed in bliss as he finally got what he’d been denied for so long. It sent an extra jolt of arousal into Dean’s gut knowing that he was the who put that imagined look on his face.

After a few moments, Dean moved his hips, letting the other man know that he was ready. Apparently that had been the signal Cas had been waiting for because after the first roll of Dean’s hips, the other man began to thrust into him forcefully causing Dean to cry out in pleasure and a low growl to rumble from Cas’ chest.

“Oh fuck!” Cas gasped, hands gripping his hips tightly enough that Dean knew he’d have bruises later, an idea that added to the mass of tingling energy in his belly. “You feel so fucking good Dean. It’s been so long but somehow it’s worth it to have this, your tight ass squeezing around my cock.”

Dean moaned at the filth pouring out of the other man then gasped as Cas pressed down on his back, pushing his chest to the mattress and changing the angle of his hips so that he was hitting that spot inside that sent bolts of pleasure right to his throbbing dick. He cried out as Cas thrust forward, relentlessly hitting that spot again and again, the other man’s left hand keeping his chest pushed into the bed while the other continued to grip his hip, forcing him to just lay there and take it.

Unable to stand the overload of sensation, Dean wriggled a hand down to wrap his hand around his aching cock; he’d only gotten one long overdue stroke before Cas roughly pushed his hand away. “Please Cas!” Dean keened, peering over his shoulder pleadingly, “Please touch me, I’m so damn close. Fuck me hard and touch me, please Castiel!”

Moaning loudly in response to Dean using his proper name, Cas used the hand pressing down on Dean’s back to start jerking him off, not slowing the movement of his hips in the slightest though his rhythm was starting to get jerky and erratic, showing just the other man was just as close as he was. Dean thrust into the warm tunnel of Cas’ hand then back onto his cock, chanting a mixture of ‘Castiel’, ‘Cas’ and ‘please’ over and over. 

“That’s it, that’s what I want to hear. Now I want you to come for me Dean,” Cas groaned into Dean’s ear, his voice wrecked and strained. He tightened his fist as he stroked Dean faster, bringing him that much closer. “Come for me so that I can feel this amazing ass clenching around my cock as I come.”

Those words along with an especially wicked twist of Cas’ hand coupled with several hard thrusts had the pressure that had been building in Dean’s groin finally snapping and he came, crying out Cas’ name one final time as waves of heat washed over him. Through the orgasmic haze he was aware of Cas letting out a loud groan that sounded something like Dean’s name as his hips stuttered against his ass. 

Cas collapsed across Dean’s back, who had already crumpled onto the mattress once his shaky limbs had given out. He couldn’t find the energy to protest being squashed, in fact, he was enjoying it in a small way so that when the other man moved to roll off, Dean may have made a small sound of protest to which Cas responded with a chuckle.

“I’m going to crush you,” he said breathlessly, flopping over on to his back. He grinned at the mock pout Dean sent his way. He patted Dean on the thigh before leaning over to grab some tissues then using them for a cursory clean up. After disposing of the tissues and condom, they both laid on the bed; neither of them spoke for a bit until Cas broke the silence.

“I wasn’t too rough was I?” Cas asked, turning his head to look over at him. Dean huffed a laugh.

“Maybe for some people but not me,” he said reassuringly, placing a hand on Cas’ chest, “That was fucking fantastic; it’s a damn shame you only get to unleash that sex beast every blue moon.”

The other man smirked smugly, preening a bit at the praise. “That’s good, I have to admit that I was worried I’d been a bit...over enthusiastic.” He glared at Dean’s pointedly wraggled eyebrows before continuing, “But I have a lot to make up for; I’ve spent literally every day you’ve worked for us thinking about how that would be so I think I’m entitled to a bit of excitement.”

Dean rolled so he was looming over the dark haired man; he smiled before kissing Cas deeply, when they broke apart, he started nibbling on the other man’s neck.

“Oh I’ll show you some excitement,” he rumbled into Cas’ ear, enjoying the groan this teased out of the man below him, “I’ll give you excitement until neither of us can walk straight.”

There was a flurry of movement and an unfortunately shrill shriek from Dean as he suddenly found himself on his back with Cas on top of him. The smoldering leer on the other man’s face caused Dean’s breath to hitch.

Cas leaned down so that his lips were hovering just of his own.

“That’s a pretty tall order. Let’s see if you can deliver.”

**Notes for the Chapter:**

> Holy moley it took me a while to get this put together. I swear, for a while there I could only write two sentences at a time, overtime at work has definitely not been doing my writing brain any favors (Oh and if anyone reading this is waiting on Awkward to the Nth Degree, I swear I'm working on the next chapter; it's just been extremely, turtle-ly slow going unfortunately). Anyway, I hope that this big block o' smut fits the bill of all of you who expressed interest in more and as always, thanks for reading :)


	3. Chapter 3

Something was going on, of that much Dean was certain.

The day had started as a typical Saturday. His alarm had gone off at six in the morning, drawing him abruptly away from a deep sleep, and he had proceeded to stumble into the shower. Once he’d been slightly more awake, not to mention clean, Dean had dressed in one of his work suits. There hadn’t been time for an actual breakfast so a hasty gulp of milk and a handful of dry cereal on his way out had been the solution. Soon he was guiding the spotless limousine up the driveway to the Novak’s mansion. Cas was standing on the front porch waiting for him.

Every weekend, Dean was scheduled to pick up his boss’ husband for his runs in the park and this weekend’s trip had started like any of the others.

Pick up Cas at the front door of the Novak residence? Check.  
Drive half an hour to the local state park? Check.  
Park the car in one of the mostly empty parking lots by the entrance to the running paths? Check.  
Wait patiently for Cas to finish his hour run? Check.  
Open the door for a sweaty, tired passenger so he can drive the other man back home?

This is where the usual pattern hit a snag.

Dean had been leaning back in the driver’s seat, looking through random things on his phone as he usually did to kill the time, when he noticed Cas emerging from the mouth of the running path. At first he hadn’t noticed the unusual fact that the other man appeared to be talking on his phone, at least not until he didn’t see the usual post run stretching begin; Dean secretly enjoyed the stretching part, all those sweat slick muscles contorting in magnificent ways, so its absence was registered very quickly. He sat up straighter in his seat, looking curiously at the scene unfolding.

Cas was clearly agitated, the hand not occupied with his phone was tugging frustratedly at his hair. His face was set in a hard line of anger as his mouth moved aggressively, obviously telling whoever it was on the phone exactly what he thought of them and Dean could tell it was not very much. He wondered what had the dark haired man so upset; Cas rarely lost his temper to this extreme level.

Except in matters concerning his wife.

_Shit_ , the chauffeur thought to himself once the pieces had fallen into place, _this can’t be good._

At first his stomach bottom fell out at the thought that Meg had learned about his and Cas’ weekend, well more like night, at the art festival but he quickly dismissed that. If the other man’s wife had an inkling of what the two of them were up to, Dean knew without a doubt that he would be dead already. However this deviation from the regular order of things had him worried because even if this didn’t have anything to do with the fact that he and Cas were sneaking around behind Meg’s back, it was definitely not going to end well.

Against his better judgement, especially considering his personal experience with eavesdropping and its dangers, Dean lowered the window, just a crack, so maybe he could hear what was being said. It worked.

“---vile bitch, I can’t believe you would sink this low. I’ve been planning this event for months---” Cas growled into his phone. Dean watched as the other man walked over to one of the decorative fences to face the woods.

There was a moment of silence during which Dean assumed Meg’s angry voice shouted from her husband’s cellphone; whatever she was saying was obviously not helping the situation since it caused Cas to reach down and grab a stone which he promptly whipped at a nearby tree. “The whole basis of this trainwreck of a marriage is that I make your frigid ass look upstanding, warm and generous and you leave me to my own devices---” Cas argued hotly, his voice getting louder and more agitated.

Silence again as Meg interrupted her husband again.

“No,” Cas said abruptly, more than likely cutting off whatever bile his wife was spewing at him. Dean was well aware at how nasty she could be, especially when she chose to press Cas’ buttons. “You do not get to call the shots because it’s your money. You wouldn’t even have gotten half the business you have if it weren’t for my ability to network---”

There was final pause as Cas was interrupted again but this time it was clear that Meg’s comment was the straw that broke the camel’s back. The dark haired man stiffened and became so still it was like looking at a life-sized photograph of him; even from all the way in the car, Dean could practically feel the arctic chill emanating from the figure by the fence, right before the tidal wave of rage erupted.

“You know what, fuck you Meg,” Cas shouted into his phone, holding the phone out in front of his face so he wouldn’t know if she was talking. The look of fury on his face was borderline terrifying. “I think I’m going to spend the day out, don’t expect me home until late.” He paused for a minute and when he started talking again, his voice had a tone of sickly sweet derision to it. “Oh, and Dean will be driving me today, I guess you’ll just have to have one of your minions haul your loathsome ass to your meeting.” 

This final remark being made, Cas forcefully jabbed his thumb on the screen to end the call and turned off the device, an angry smirk on his face. He turned and stalked towards the car where Dean was waiting anxiously.

Unable to pretend that he wasn’t listening, Dean opened the door and emerged from the car. He leaned against the closed door and waited for Cas to get to him. Anger and frustration was still coming off the other man in waves.

“So uh, what was all that about?” Dean asked hesitantly, hoping that he wasn’t about to make things worse. His hands twitched at his sides, wanting to reach out and attempt to soothe but he resisted, not sure if the gesture would be appreciated. 

There was also the fact that they were in public, granted they were basically alone in the middle of the woods, but it was still a public place. At least Dean thought that was an issue, right up until Cas pressed him up against the car, attacking him with his mouth and pulling all the air out of his lungs.

It took Dean a minute to get up to speed with what exactly was happening, the way Cas’ tongue forced his teeth open to deepen the kiss while the other man’s knee parted his legs had him more than a bit distracted but, once his brain registered that that heat at his back was the metal of a car door and that they were still out in the open, Dean pushed Cas away. They were both panting hard and the other man immediately began tried to bring Dean back to him.

“What are you doing?!” Dean whispered as if to discourage eavesdropping from the vacant area surrounding them, trying to nudge Cas backwards so that his attention was pulled away by the feel of the other man’s muscular thigh against his groin, his dick twitched in response to the pressure and friction. “We’re in the middle of a parking lot. Someone could see us.”

Cas huffed in annoyance, moving back in so he could nip and suck at Dean’s neck; the sensation sending a shiver across the chauffeur's skin when warm breath tickled spit slick flesh. “I don’t give a shit,” Cas growled into his jaw, “I’ve had it up to here with today and that gorgon of a woman I’m married to so I am going to bend you over and fuck you until you can’t walk straight.”

He emphasized his point by grinding his hips against him; Dean gasped, his own hips betraying what was left of his rational mind by bucking upwards. Cas laughed darkly and repeated the motion.

“Let’s move this to the backseat,” he rumbled in Dean’s ear before nipping at it as he pulled away. Against Dean’s better judgement, which was chattering in the back of his mind about how he should put a stop to this, he allowed himself to be manhandled into the backseat; the rough treatment had him hardening in his dress slacks already. 

Once they were in the backseat, Cas began to tear at the clothing separating him from Dean’s skin, all the while their mouths moved together frantically, and soon they were both bare chested; Cas pushed him down so that he was spread out over the spacious bench seat with the other man on top of him; Dean took the opportunity to slide the sweat damp t-shirt over Cas’ head so he could run his hands over the other man’s back, feeling the hard muscle shift under his palms. 

The dark haired man abandoned the chauffeur's mouth, much to Dean’s chagrin, in order to kiss his way down Dean’s chest towards his belt. As Cas got closer and closer to the bulge in his slacks, Dean began breathing even more heavily. He prayed that this was headed where he thought it was and then as if he had heard his thoughts, Cas hurriedly undid the button and zipper of his pants. 

Dean groaned as his hard length was exposed then nearly choked on air when he found himself being unceremoniously swallowed down once his pants had been ripped off his legs, leaving him naked. His hands scrabbled on the upholstery, desperately trying to ground himself against the burst of sensation of Cas’ tongue swirling over the head of his cock. Hips pinned to the seat by strong rough hands, Dean had no choice but to lay still and surrender as he was slowly brought to the edge then backed down time and time again during the exquisite torture that was Cas’ mouth.

After several minutes, he risked a peek downwards and almost came on the spot as Cas’ heated blue eyes met his. Dean couldn’t resist reaching down to tangle his hand in the dark nest of hair bobbing up and down in his lap. 

“I thought--thought you were---going to fuck--me,” he managed to pant out, most of his brain occupied with not coming too soon as Cas pulled off of him and started nipping at his inner thigh. Dean yelped the slight pinch of a particularly rough bite, causing the other man to laugh.

“Don’t worry handsome, you’ll get this cock when I’m ready to give it to you,” Cas rasped, voice hoarse from the blowjob he’d been performing. Dean may have whined a bit, knowing that the dark haired man meant to make him work for it.

Suddenly the weight on his legs was gone, he looked down to see Cas rummaging under the seat of the car. Dean leaned over to look at this sight with curiosity, wondering what the hell the other man was up to when Cas emerged with a grunt of triumph, a bottle of lube and a condom in his hands.

Dean wanted to ask where these items had appeared from but was cut off by the bottle of lube being tossed at his chest. 

“Get yourself ready for me,” Cas ordered, seeing Dean’s look of confusion. The dark haired man was sprawled on one side of the bench seat, facing the chauffeur as he slowly lowered the band of his workout shorts over his dick so it rested below his balls; he began to tug leisurely on his hard length, keeping his gaze fixed on Dean. His eyes were blown wide with lust and he gazed at him while stroking himself lazily. “I want to see you stretching yourself for this thick cock and once you’re ready, I want you to ride me.”

Considering how many times Dean had fantasized about this very scenario, riding Cas in the back of the limo, it wasn’t surprising that he threw himself eagerly into the task of slicking up his fingers and slowly working them inside. Normally Dean would have rushed through this step as much as possible in order to get to the good part but something about the hungry way Cas looked at him while slowly stroking his own hardness had him wanting to put on a show. He slowed his movements to a tortuously slow pace, making sure to throw his head back and expose the long line of his throat, an area he knew from experience was on of Cas’ favorites.

“Oh god,” Dean moaned, his fingertips were prodding his prostate on the inward push of his hand and it had him screwing his eyes shut at the bursts of pleasure. 

“Look at you my little slut,” Cas’ deep voice filtered into his ears through the haze of sensation. “Riding your fingers like that. I bet you’re imagining that they’re me but they aren’t enough are they? You need something else, something bigger; you need my hard cock splitting you wide don’t you?”

Gasping slightly as Cas’ words sent a wave of heat to his belly, Dean forced his eyes open to look down where the other man was seated. The sight of Cas watching him, looking like he was one minute away from pouncing and fucking him into oblivion was the final straw.

“Please, please sir, I need it,” Dean whined, hoping to force the other man into action, his hand still working between his legs. “Need to feel you pushing into me, filling me up. Please!”

The plea worked; the final please was barely past his kiss swollen lips before Cas hurriedly rolled on the condom and roughly dragged him into his lap. Dean settled himself on top of the other man, leaning forward to kiss him hungrily. Cas’ hands skimmed up and down his back before travelling down to knead the muscles in his ass; the dark haired man’s fingers dipped in to toy with his prepared hole, forcing a series of breathless moans from him.

Unable to take the teasing any longer, Dean reached back to grasp Cas’ cock and shifted so he was positioned above it. Cas was looking up at him, the blue of his eyes practically nonexistent with how blown wide his pupils were, his mouth parted in anticipation. Neither of them breathed for the moment before Dean started to carefully sink down onto the hard length beneath him but this silence was quickly broken by deep moans as they both finally got what they wanted so badly.

Once Cas was fully inside, Dean paused for a moment to adjust. The other man’s head was thrown back against the seat and he was panting and shaking with the restraint it took not to move yet. Deciding to blow said restraint out of the water, Dean braced his hands on the seat on either side of Cas’ shoulders and began moving his hips, going from zero to sixty in practically no time at all.

“Shit! Oh, fuck!” Cas gasped, his head shooting upright, looking at him with widened eyes. Dean chuckled at the shocked expression and put that much more effort in rolling his hips, enjoying the power of taking the other man apart. 

Hot hands gripped his hips tightly but did nothing to impede his movements. After several minutes of moving up and down in Cas’ lap, Dean shifted his hips just so and his rhythm stuttered as the dark haired man’s cock his his prostate. Blinded by the feeling, Dean repeated the action again and again, the tightness in his groin being increased with each movement and by the gasps and moans of the man beneath him. 

“That’s it Dean, ride me,” Cas managed to pant out, bucking his hips up as much as he could in this position. “Fuck yourself on my cock, just like you were made to do. You’re my pretty slut aren’t you Dean? Only mine.”

“Yours, only yours,” Dean groaned, grinding down hard as he chased his release, his hands gripping the other man’s sweat slick shoulders. “Your pretty cockslut, Castiel.”

This last statement pushed Cas over the edge and he came with a deep groan, bucking his hips up hard into Dean and biting down on his shoulder. The sight of the dark haired man falling apart coupled with the rough thrusts had Dean’s own orgasm bursting out of nowhere, surprising him as he came untouched between them with a choked gasp.

Dean slumped over and rested his head on Cas’ shoulder as they sat there, trying to catch their breath. The air in the back of the car was hot and thick from their escapade but soon the chill from outside began to creep in and Dean shivered when it hit his sweat covered skin. Cas shifted a reluctant Dean off his lap long enough to remove the condom, halfheartedly wipe off their stomachs and grab the chauffeur’s discarded suit jacket. Once the other man had them laid out on the bench seat with Dean on top of him, he covered them with the coat.

“So really, what was that all about?” Dean asked several minutes later. They were still laying in the back seat of the car; Cas was trailing his fingers up and down the skin of Dean’s arms while Dean was dangerously close to falling asleep.

Sighing, Cas turned his head to look at him, his expression was one of resignation. “Oh the evil hag decided she no longer wants to host the event for a charity of mine that I’ve been planning for months, deciding that the needy don’t really need our money or our help,” he said with more than just a touch of anger. “Apparently there is a ‘very important meeting’ and it’s going to cost a lot of money to arrange so there’s no room in the budget for a charity event.” It was obvious this was something very important to the other man and it saddened Dean that Meg couldn’t let Cas have it considering how little freedom the dark haired man had and it pissed him off since he knew the bitch probably cancelled the event on purpose. 

As if the Novak’s didn’t have enough money, what a load of shit.

Dean tilted his head up and kissed the other man’s jaw. “I’m sorry about your charity thing,” he said apologetically, running his hands over what skin he could reach. “So you decided the best way to get back at her was to fuck me into the limo?” Dean continued, hoping to lighten the mood.

Cas smiled and laughed quietly. “Well, I hadn’t exactly planned on it,” he answered, “But I suppose it will make riding around with her easier knowing that she’s sitting in the very spot we fucked in.” There was a pause and then he laughed again, this time hard enough to jostle Dean. “And with her lube and condoms too.”

Curiosity peaked, Dean looked up at him questioningly. The other man explained that, since his wife was free to take lovers as she chose, Meg kept a stash of condoms and lube in the car. Apparently this wasn’t the first time someone had gotten laid in the back of this limo. To prove his point, Cas rummaged around on the floor for the bottle and showed it to Dean. That was when he noticed that the bottle was light pink and labelled ‘K-Y Mine’.

“Oh, so that’s where the supplies came from. I was going to ask about that,” Dean said, the light bulb clicking on in his head as he remembered where he’d seen that bottle design before. His head shot up in surprise as another realization hit him, “I thought that stuff was tingling a bit but figured it was just in my head or that your crazy sex mojo had finally fried my brain.”

This last statement had Cas laughing so hard Dean was forced to hold on so he wasn’t jolted off of the man below him, causing the chauffeur to chuckle a bit too.

“Thank you Dean,” Cas said as he got himself under control, wiping tears from his eyes and looking down at him with a surprisingly soft expression. “I really needed that.”

Deciding to be a smartass, Dean responded with a grin, “The hardcore sex or the comment about the lady lube?”

Cas kissed his smirking mouth before replying quietly, “Both.”

**Notes for the Chapter:**

> A little bit of fluffiness snuck its way in there at the end but if there's anything to be learned about me by this point, it's that I can't resist a bit of warm fuzzy feelings when I write. Hope you guys enjoyed the smut too. :)


	4. Chapter 4

“Oh shit Dean, yes!”

The chauffeur hummed happily around the length in his mouth, preening at his ability to turn his normally confident and suave lover into a quivering mess. Usually he was the one panting and gasping, writhing wantonly against the other man in desperation but not today. Strong fingers wound themselves into his hair and gripped tightly, sending a jolt of pleasure to Dean’s already throbbing cock. He reached a hand down to free himself from his slacks so he could stroke himself as he continued to mouth at Cas’ dick.

“God, that mouth,” Cas groaned as his hips twitched up into Dean’s face minutely, “It was made for sucking someone off.”

Dean pulled off for a second to catch his breath, pressing kisses to the hardened flesh. “Only for you,” he muttered, his voice raw from deepthroating the other man. 

This declaration pulled a moan from Cas and had the other man tightening his grip on his hair, pulling his head insistently back to where it had been. Dean complied willingly, eager to get back to work, and took Cas into his mouth again.

As he resumed his rhythm from before, Cas leaned heavily back against the concrete wall of the building they were currently behind.

Dean had driven Cas to one of his favorite books stores that morning to buy a specific book but when the other man had gone inside, all the copies had been sold. When he had made his way back to the car to find Dean leaning against the car door waiting for him, the other man had told him what had happened and shamelessly hinted that he could be made to feel better if only someone were to give him an impromptu blow job.

Like Dean could say no to that. 

Which is what led them here with the chauffeur on his knees in an alley, hidden behind a broken down van with Cas’ cock in his mouth and a hand on his own dick.

He’d never been much for exhibitionism but the fact that they were doing this in broad daylight had Dean more than a little excited and if the amount of precome Cas was dripping was any indication, it also go the other man’s motor running too. Knowing they did have a time limit, Dean knew he needed to step up his game so taking a deep breath, he slowly sank down until the tip of Cas’ cock brushed the back of his throat and swallowed.

Cas gasped, his hand sliding down to cup Dean’s hollowed cheek. The chauffeur looked up to see the other man looking down at him, his eyes looking dazed with the amount of pleasure he was giving him. “What did I---ever do to deserve you?” he panted, brushing his thumb over Dean’s cheekbone, “You’re so fucking good for me.”

The praises pouring out of Cas’ mouth and soft touches, along with the sight of the other man looking so debauched and aroused, went straight to Dean’s groin and the hand grasping himself sped up as he unconsciously chased his own release but he forced himself to ignore the tingling urge to jerk himself frantically until he came; this was about Cas. Slowing his hand down so the tightness in his lower belly was at a slow burn, the chauffeur redoubled his efforts in pleasuring his lover. The tight grip on his hair and the aborted jerks of the other man’s hips told him it wouldn’t be long now.

It was time for the big finale.

Dean pulled off briefly, causing Cas to groan in protest but this sound of disappointment quickly turned into one of enjoyment when the chauffeur whispered, “Fuck my mouth, Cas,” before taking him back in.

“Fuck, so perfect,” Cas grunted as he eagerly complied with the request as he wasted no time in pulling Dean’s head into his groin and then pushing it back. He quickly built up a punishing rhythm but Dean couldn’t care, he was too distracted by the sight Cas’ head thrown back against the wall, mouth open in a silent scream of pleasure as he took what Dean had offered. The chauffeur’s cock throbbed urgently and, unable to resist any longer, he hurriedly tugged at himself, needing to come so badly it felt like he’d spontaneously combust if he didn’t soon. 

“Are you going to--c-come for me Dean?” Cas asked breathlessly, looking down with heated blue eyes to see Dean’s hand working frantically between his legs. Dean met his gaze and hummed in response with a slight nod of his head. Cas growled and took a firmer grip on his hair, hips jerking up harshly, “Good, I--I want you to come just like this, my thick cock down your throat while you jerk yourself off because you’re a slut for having my dick in your mouth aren’t you? You’d do this every day if we could and it still wouldn’t be enough for you, you’d need more. And I would be happy to give it to you because I love this hot, wet mouth...oh...oh fuck!”

Cas groaned deeply as he pulled Dean’s face as close as possible as he came; Dean could feel the other man’s cock throb immediately followed by the splash of come at the back of his throat. The chauffeur forced his gag reflex to relax so he could swallow it down before pulling off with a gasp as his own forgotten orgasm hit him like a freight train and he came in spurts on the ground beneath him. Cas lowered himself so that he was crouching by the wall in front of Dean, his legs shaking slightly.

They both panted for awhile before getting their breathing under control as they tucked themselves away. Eventually, once they’d righted their clothing, Cas stood up and pulled Dean with him so they were leaning heavily against the wall, the chauffeur pressed against his chest. He ran a hand gently over Dean’s back.

“That was fantastic Dean,” Cas said after a few minutes of silently absorbing each other’s presence in the afterglow, “And normally I would love to take the time to show you just how much appreciate this but we have a schedule I believe.”

Dean groaned, annoyed that reality was once again reinstated but knowing that the other man was right. He checked his watch and sighed, “You’re right, I have to ferry the hag to an important meeting here in an hour. I’ll have to drop you off at your house and fill up the car before I go to pick her up.”

Nodding in reluctant understanding, Cas started to lead them back to where the car was parked, “Yes, she’s been talking about that all week. I only know because that meeting means I get to go and represent ‘us’,” the other man said, putting air quotes around the word, “At a charity event tonight.”

They approached the car and resumed their usual places, playing the part of the rich boss riding in the back of the car with Dean dutifully in the front but the chauffeur knew it was only acting. If things had been different, something that he found himself musing about more and more often anymore, he could see the two of them in his own car, driving home to continue what they started in the alley. 

But things were the way they were and he and Cas would have to take what little they could get.

There was no more talking as Dean drove the car back to the Novak mansion though he did receive a soft smile when he opened the door for Cas to emerge; it was discreet of course, taking into account the multitude of security cameras and guards that dotted the estate, but it made a warmth settle in Dean’s chest and that was enough for him.

Once Cas was inside the house, Dean drove to the gas station to fill up the car and made it to Meg’s office almost exactly on time to pick the woman up. He’d barely put the car into park before he saw the petite brunette walking briskly out of the double glass doors and had to scramble as discretely as possible to get to the back passenger door in order to open it for her promptly.

As usual, she didn’t acknowledge his presence but he was used to it by now so he carefully shut the door and took his place behind the wheel and after a cursory check that they were ready to proceed, via the intercom of course, they were on their way. All in all it was a textbook normal day.

So Dean was completely shocked when the partition was lowered.

At first Dean was only surprised at the disappearance of the barrier separating him from his passenger, part of him was thinking back to the first night with Cas and foolishly thought this was going to be a repeat but then he remembered who he was driving around at the moment.

His stomach immediately began to tighten with nerves.

Reminding himself to keep calm, he took a deep breath and, trying to sound normal, asked, “Yes Mrs. Novak? Is there something wrong?”

“Yes, there is,” Meg’s voice said neutrally from the back. Dean felt cold sweat break out on his neck and under his arms.

They had been caught, she knew about him and Cas. This was it, he was going to die.

Dean worked desperately to control his breathing and his panic, it wouldn’t do him any good to freak out now. Maybe if he insisted he didn’t know anything he would be okay. He took a deep breath and squared his shoulders, waiting for the hammer to fall.

“The venue for my meeting has changed,” his boss continued calmly. There was the shuffling sound of movement behind him and a piece of paper held by manicured hands appeared next to his head. “This is the address, can you find it? I don’t want to be late.”

The wave of relief that washed over Dean was so great, it took all he had not to slump over and laugh. Instead he carefully took the paper and looked at the address. It was an office building about eight blocks from where they were supposed to be going tonight, easy enough to find.

“Yes ma’am,” the chauffeur responded professionally, “I know where that is, I’ll have to park the car in the parking garage across the street though, Mrs. Novak. There’s no parking allowed on this area of the street.” 

“Yes, yes, that’s fine,” Meg responded airily, probably already moving on to other business on her phone, “I don’t care, just get us there on time.”

The partition closed and once it was in place again, Dean allowed himself a sigh of relief. 

He was just being paranoid, probably because what he and Cas had been up to this afternoon was still so fresh in his mind. That was all. Meg still thought his was just another part of the car, not an actual human being.

Shaking his head at his easily spooked mind, Dean focused on finding the new building so that his boss wouldn’t be late for her precious meeting.

 

They arrived at the address on Meg’s paper about five minutes early. It was starting to get a bit dim out in the early evening light so Dean flipped on the headlights.

Dean pulled the car next to the curb and, after putting it in park, stepped out to open the door for his boss. He opened the door and extended a hand to help her emerge from the car. She made her way towards the door without a word or a glance as usual so he moved to get back into the car. The car would need to be moved to the parking garage where Dean would wait until Meg summoned him to take her home. 

Luckily he had just charged his phone so he could at least play games and surf the internet. These meetings could be very long sometimes.

It was just a he was opening the driver’s door when Meg’s voice echoed across the sidewalk. 

“Winchester!” she called in annoyance from her position by the building doors, “I forgot my bag, bring it here,” she ordered imperiously.

Used to such orders, Dean repressed a huff of agitation and walked over to open the back passenger door where, of course, Meg’s bag sat on the seat. Schooling his face into one of neutrality, Dean grabbed the bag and walked briskly over to where Meg stood with her ever present bodyguards. He never understood why she always had him bring her forgotten items when she always had these two lugs around, she should make them go get her things all the time.

He handed over the expensive leather bag which the woman took without even a nod of acknowledgement before she turned towards the doors to go inside. Dean turned on his heels to go back to the car.

“Oh, one more thing Dean,” Meg’s sickly sweet voice said suddenly behind him. Dean froze, unable to breathe, at the use of his first name. This was an unheard of occurrence. “I know you’ve been fucking around with my husband.”

Dean barely had a minute to register the fact that his guts and legs had turned to water before a sharp pain burst across the back of his skull and everything went black.

**Notes for the Chapter:**

> I know, a cliffhanger, how evil of me but I should have the next chapter up very very soon. Cross my heart.


	5. Author Note: Please Read First

Okay so, hopefully you've read chapter 4 and are of course angry that me for that cliffhanger but I have a way to make it up to you all for you see...I wrote two endings to this story.

*Cue dramatic dun-dun-dun music*

I've spent ages agonizing over how I want this next bit to play out and I had two very different scenarios but I was having a very hard time picking one so...I didn't.

The next two chapters of this story are the two different endings of this story and, for being such a fantastic group of readers, I leave it up to you as to which one you'd like to read.

Ending A is for those of you who, like me, enjoy a good old fashioned happy ending.

Ending B is for that small part in all of us that craves a bit of sorrow in our stories.

For those of you who are daring enough to read both, let me know which you liked better since I'm a bit curious see which ending everyone prefers. I await your opinions eagerly.


	6. Ending A

**Notes for the Chapter:**

> Hello, if you haven't read the previous chapter, you might want to back track and take a look, just so you have an idea of what madness I'm up to here.

A sharp slap to the face is what brought Dean back to the land of the living.

“Wakey, wakey Winchester,” a deceptively sweet voice cooed, the sound of it forcing its way through the dizzy haze in his head. Dean blinked his eyes open, hissing as bright light seared his retinas; he tried to reach up to rub at his eyes but was stopped. Looking down he saw he was tied to a chair. “Ah, there we are.”

When the blurring of his sight subsided, Dean could see that he was face to face with Meg.

The moments preceding his blackout came to him in a rush and as he remembered why his boss was looking at him with a razor sharp smile and narrowed eyes, his heart began to pound.

Meg knew about them.

From the looks of things, Meg had moved them to her office downtown if his vague memory of that fateful interview for the position as the Novak’s chauffeur was anything to go by. Meg leaned back against the elegant wood desk behind her, bracing her palms on either side.

“How are you feeling Dean?” the woman continued in her mockingly concerned tone. She forced her face into one of worry, “That was a pretty hard blow Rocko gave you, would you like some ice? An ibuprofen? My husband’s cock in your ass?” This last was said with the same air of deceptive calm but Dean could see rage flashing in his employer’s eyes.

“Listen I don’t know--” the chauffeur started to deny, hoping that if he acted as if all of this was a big mistake, maybe the violent woman in front of him might believe him. He didn’t put much stock in the plan but it was the only one he had; unfortunately Meg cut him off before he could really get a handle on playing the offended victim.

“I have video,” she said abruptly, leveling him a look at Dean that just dared him to interrupt or contradict her. Meg reached over and picked up the phone lying on the desk, thumbing through the screen before tapping it; she turned it around to show the screen to Dean.

What he saw there made his blood run cold.

It was him and Cas, in their motel room at the craft fair. The video must have been from the morning they left. Dean had wanted to get on the road but Cas had pouted until he’d agreed to one last romp before they checked out. The other man had pushed into him slowly, pressing Dean into the bed and proceeded to fuck him slowly and almost tenderly. 

It was one of Dean’s favorite memories, that whole weekend was really, and now it was tainted forever by the knowledge that someone had been watching them the whole time.

_Well,_ he thought sadly to himself, _at least the memory won’t be tainted for long, I doubt I’m going to be around to think about it for much longer._

Meg let the video play, the sounds of gasps and moans and the sound of skin on skin sounding extremely obscene in the current location, until the Dean and Cas on the video cried out in pleasure as they came, only then did she switch the device off.

“I’ve got hours of that on tape,” his boss said, casually placing the phone done and meeting his eyes. She started to pace slowly back and forth; Dean’s gaze followed her warily, wondering what her endgame was. “I had had my suspicions about Castiel and had an associate of mine who owns the hotel you stayed at bug your room for me. At the time I thought my husband planned to seduce you, since I was under the impression that you were straight, and planned on using the video as part of a lesson for him but from the evidence I can see that you were just begging for it.”

Walking around the enormous desk, Meg settled primly in her plush executive style chair and crossed her legs. The room fell silent as she considered him, the touch of her gaze made Dean want to shudder but he refused to give her the satisfaction.

“How long have you been screwing my husband?” she demanded sharply. The toying portion of the conversation was obviously over, judging by the hard glint in his boss’ eyes. “And don’t bother lying, it won’t do you any good; in fact I might just make you suffer more for it.”

Dean chewed on his lower lip, considering his options.

Option A was to lie his ass off. Claim that the incident in the hotel was the only time, that Castiel forced him into it, that he decided that it was too dangerous to attempt again and pretend that he regretted sleeping with her husband, that Cas meant nothing to him. If he begged and pleaded enough, Meg might let him go.

If Dean were a coward and a piece of shit, he would pick Option A to save his ass.

But Dean was not a piece of shit, not to say he wasn’t scared, so he was going to go with Option B, something he knew would most likely get him killed on the spot but would sit well with his conscience. 

He took a fortifying breath and brought his head up to look Meg in the eye. “About a year,” he answered evenly. Dean was surprised at how steady his voice was; it was like was he were ordering a coffee at the gas station, not staring down his boss who just happened to be a crime lord.

“And what possessed you to not only sleep with a married man, but with a man that belongs to me?” Meg asked, her voice starting to get sharp, she leaned forward and put her hands on the table, “Did you and that faggot husband of mine get a big laugh out of making me look like a fool? At possibly ruining my reputation? Did you?” Her tone got more and more shrill as she talked until the last statement was practically shrieked.

Resigning himself to was most likely going to be a painful death, Dean answered truthfully. “Honestly Meg, it wasn’t about you,” he said firmly, anger starting to tinge his own words as frustration on Cas’ behalf began to overpower the fear for his own life, “It was about spending time with a man who was lonely, a man who you forced into isolation because you were afraid for your reputation. It was cruel of you, parading your partners around under Cas’ nose while he was constantly reminded that if he even tried to have someone of his own you would rip it all away, all the while reaping the benefits of his presence by your side. He’s a good man and doesn’t deserve to be alone forever.”

Though now, if Cas managed to make it out of this mess unharmed, he would be. Dean certainly wasn’t going to be around after that little rant.

Meg hadn’t been expecting this and glared at him angrily. “Castiel,” she sneered, curling her lips around the name in disgust, “Only deserves what I give him and he’ll be lucky if he gets out of this without me removing parts of him he’d rather have attached; my husband will have to earn my trust back. But first,” his employer paused to press her finger to the intercom, the harsh buzz of it followed by the opening of the large heavy oak doors, “He must be taught a lesson.”

As Meg stopped speaking, two thugs dressed all in black burst through the doors dragging someone between them. They heaved the person up by their armpits and threw them into the chair next to Dean. While the bodyguards were zip tying the man’s arms to the chair, Dean realized it was Cas they were binding up.

The muscle-bound thugs finished securing Cas, who was still looking around groggily, to the chair and then maneuvered the two captives so that they were facing each other. Cas’ head was laying on his chest and Dean wasn’t sure if he was even conscious anymore but could at least see from the slight movements in the other man’s chest that he was alive; this confirmation had a relief washing over him.

Cas was okay, for now anyway.

Dean was brought back current affairs when Meg walked around her desk, a glass of water in her hands; she looked down at her husband, her nose wrinkled in disgust, and tossed the contents of the glass on him. Cas jerked and sputtered, water splashing the side of his face.

The other man looked around wildly, taking in his surrounding before his eyes settled on Dean. His gaze softened for a millisecond before falling into an expression of fear. “Dean,” he breathed.

Meg clapped her hands loudly, sighing as if this were one of her meeting and the last participant had finally arrived after being late. “That’s better,” she said brightly, ignoring the fact that half her audience was tied to chairs, “Now that we’re all together, Castiel’s lesson can begin.”

“Meg, wait--” Cas protested, only to be rewarded with a swift blow to the jaw by one of Meg’s bodyguards. The other man spat out some blood onto the pristine carpet, the bright red standing out on the material.

“No, Castiel,” Meg ordered firmly, she reached down to tightly grip her husband by the jaw causing him to flinch when she dug her fingers into the area where the thug had hit him. She forced his head into an uncomfortable angle so his eyes were in line with her’s. “I warned you about the consequences of straying a long time ago and now you have to live with the result. Maybe if I make you watch, you’ll think twice before you disobey me.” Roughly releasing him, Meg turned to the men and nodded.

That nod was apparently the signal to begin beating Dean within an inch of his life.

Fists like hammers fell onto his face causing pain to burst across his mouth, nose, jaw and eyes while other blows found their way to the soft flesh of his stomach, knocking the wind out of him while others hit him in the ribs. It was all a bit of a blur; he could dimly hear Cas yelling, telling Meg to stop, that it wasn’t Dean’s fault but his own. Somewhere in the part of Dean’s mind that wasn’t currently howling in agony, he appreciated the effort on Cas’ part, at least, until someone brought a tire iron into the mix and used it on his knees and legs. 

Dean was unashamed to say he cried after that.

Finally, as suddenly as it began, it stopped. Dean gulped in air in harsh pants, flinching when this motion irritated the sharp pain in his ribs; some of them had to be at least cracked, if not broken.

“That’s enough Meg,” Cas growled, tugging his bindings. From the little Dean could see of him through his swollen eyes, the other man was attempting to sheer rage to escape his bonds but unfortunately was getting nowhere. “I’m the one who fucked up, I’m the one who should be punished. Let Dean go.”

Meg chuckled lowly walking over behind Cas; she crouched down so her face was next to his and smiled. “Oh but you are, Castiel,” she cooed sweetly, brushing a hand down his cheek. Her dark eyes, looked up at Dean, a sinister glint to them. “You are the one who will be punished. This is your punishment, to watch what I do to your little boy toy and know that not only is it entirely your fault but that this all could have been prevented if you had kept your dick in your pants.”

The woman stood up and walked over to Dean, holding out her hand to one of the guards as she went. One of them handed her the gun from his shoulder holster. Cas’ eyes went wide and he met Dean’s gaze as they both realized what was going to happen at the same time.

Cas was going to have to watch as his wife murdered Dean.

The other man began to thrash wildly, pulling desperately at his bonds and shouting curses and pleas at his wife as she slowly walked over to stand behind the former chauffeur. Dean shivered as cold metal pressed against the back of his skull.

This was it then.

“Cas,” Dean said softly, interrupting the flow of anger, frustration and fear issuing from the other man. Cas fell silent and looked at him, chest heaving and eyes wide in panic. “It’s okay Cas, I’m fine. I don’t blame you for this.” He stumbled over his words, trying to get them out before Meg pulled the trigger. “I knew what I was signing up for and I wouldn’t change it for the world.”

Tears shone in Cas’ eyes and he resumed his squirming, still trying to break free. “I’m sorry Dean, I’m so sorry,” he whispered back, voice choked by his emotions, “I never wanted this to happen.”

Dean was about to reassure him again when the harsh voice of Meg interrupted him. “Oh my, how sweet is this,” she cackled. The chauffeur couldn’t see her face but he knew she was sneering. “I really should tape this, it’s an Oscar worthy performance but sadly I don’t have the time. I have another meeting in ten minutes so say---”

The tinkling crack of broken glass was the only warning before Meg shouted in pain. Dean felt something warm rain down on the back of his neck then heard a thud behind him and saw the bodyguards in front of him move to rush forward but suddenly red dots appeared on their chests and before either of them could think to move, they collapsed instantly in bursts of blood.

There was barely time to process what had happened before the doors to Meg’s office were opening and three heavily armed men entered, followed by a shorter man in a dark suit.

“Well, what have we here,” the new comer, a man short dark hair and scruff, mused in a deep, rumbling voice. The man had a slight British accent. He seemed unfazed at finding the two of them tied to chairs. “Let’s get you boys out of those chairs shall we?” 

The man walked over briskly, grabbing a sharp letter opener off of Meg’s desk as he went and proceeded to slice the plastic ties holding Cas in place. The instant he was free the dark haired man was over by Dean’s side, running a gentle hand over his face.

“Oh god, Dean,” he whispered between placing very delicate kisses on Dean’s battered flesh. It stung slightly but right now it was the best feeling in the world to Dean. “I’m so sorry, please forgive me.” He continued this pattern of apologizing and pleading for forgiveness between hesitant touches and kisses until he was interrupted by the mysterious stranger.

“This is all very touching and all Castiel but I feel the best thing for your little friend here would be for you to move aside so I can untie him. It will be easier to get him some medical assistance that way,” the man drawled, his tone indicating that he found Cas’ actions slightly annoying.

Cas quickly pulled back and let the other man work but was unable to stop himself from leaping forward once Dean had been freed. He gently helped him to his feet and together they turned to face their rescuer. “Thank you Crowley,” Cas said, not bothering to hide the relief in his voice, “Thank you.”

“Oh no, thank you Castiel,” the man, Crowley, replied with a half smile that didn’t really touch his eyes, “Thank you for turning over your wife’s,” he paused and looked down to where Meg’s body lay in a pool of blood, “Sorry, ex-wife’s business holdings to me. It’s been a pleasure doing business with you. I’ll have my people take care of this mess, as per our agreement, and as an added bonus for this deal going so smoothly, I’ll have one of my boys drive you home.”

Nodding in agreement, Cas held out the hand that wasn’t helping to support Dean and he shook hands with the other man. Crowley snapped his fingers and one of the silent guards walked over and helped Cas carry Dean out of the room and down to a car that was waiting at the curb. The two of them were deposited in the back and promptly driven to the Novak mansion. The bodyguard even helped to get Dean into the house.

Dean had so many questions but waited until Crowley’s man was out of the house before pouncing.

“What the fuck just happened?” he asked from the sofa, a remarkable amount of calm in his voice considering the evening he just had. Cas walked over to the sofa with a first aid kit and began to tend to Dean’s many wounds.

“I made a deal,” Cas said simply. “I’ve known for years now that Crowley wanted to take Meg’s business for himself and when my wife told me tonight that she knew what we’d been up to, I made a phone call. She always did underestimate the importance of my ability to network.”

Dean could tell there was more to the story and raised an eyebrow questioningly, hissing slightly when the other man hit a particularly tender area. “So a phone call, that was it? One phone call and this guy busts in to save our asses?”

“Apparently so,” the other man replied, “To be honest with you it was a desperate play but I had no choice. She had you Dean and she knew; I was already on lock down and I needed help quickly.” Cas’ voice held more than a few notes of fear, those blue eyes glazed over as he relived past panic. “Unfortunately for her, her stupid guard forgot to take my phone. I promised Crowley if he helped me save you and get rid of Meg, he could have all of Meg’s criminal organization. I would keep the legitimate part of the operation and operate as a smoke screen for him. It seems the deal appealed to him.”

He helped Dean up from the couch, saying that it would be best if he lay down on the guest bed to get some rest. Together they hobbled to the guest room and Cas gently helped Dean remove his bloodstained clothes down to his underwear and up onto the bed to stretch out on the plush mattress. Eyes heavy with adrenaline rush induced grogginess, Dean watched as the other man slowly and tiredly stripped himself down to his own boxers before climbing into bed and drawing the duvet over them.

Normally Dean would be jumping at the chance to plaster himself to Cas’ side but the sad fact of the matter was his body was in no shape for that so, as if sensing his predicament, the other man slid over to gently curl up against his side. The slight ache the dark haired man’s head resting on his shoulder was an easy price to pay to have Cas close to him.

Neither of them spoke for a while but they didn’t succumb to the need to sleep either, the terror of the past few hours was still too fresh in their minds.

“Are you truly okay Dean?” Cas said suddenly, his lips brushing against Dean’s skin, “I understand if you don’t want to see me again, what I put you through---”

Dean cut him off, leaning down to hush him with a kiss; pain be damned. “I meant what I said Cas,” he muttered softly into the other man’s hair, “I don’t blame you, this is all on that evil bitch. And...well, since it’s just us now and there isn’t a gun to my head, I want you to know that...I love you.”

Cas stiffened at his side and Dean’s stomach tightened horribly.

Maybe he should have waited to tell Cas he loved him. It had been a very chaotic day and they’d both been through the wringer, maybe declarations of love were just too much for today.

There was a shuffle of movement as Cas raised himself up onto his elbows to look down at Dean’s face, his expression surprised.

“Do you really mean that?” he asked, a small bit of awe creeping into his voice. The other man looked like he couldn’t believe his ears and that made Dean’s heart hurt a little. How could Cas think that Dean loving him was so amazing?

Nodding firmly despite the ache in his head, Dean answered firmly, “Every word. You mean the world to me Cas.”

All the pain and agony in his body was pushed to the far corners of his mind as Dean witnessed Cas face light up like Christmas morning. Those blue eyes that he loved so much were brimming with happiness and it made Dean’s own chest feel like there was a warm sun buried there. This feeling was heightened when Cas leaned down over him and brought his mouth to Dean’s, being careful not to aggravate his injuries.

After a few gentle and chaste kisses that left Dean’s head spinning in a way that had nothing to do with his potential concussion, Cas pulled away and buried his face in Dean’s neck.

“I love you too Dean,” he said quietly, rubbing a hand over an unmarred area of his chest. “And once you’re all healed up, I plan on showing you just how much you mean to me.”

Dean chuckled as much as he was able to with his injured ribs. “Already planning on our next romp in the sack Cas?” he questioned teasingly, “My my, you just can’t get enough of me huh?”

Cas response, mumbled sleepily into the skin Dean’s collarbone, would have floored him if he weren’t already laying down.

“No, I’m talking about our wedding.”

Once Dean was able to think again, he smiled so much it hurt his mouth but he couldn’t be forced to care; he just pulled Cas tighter to his side, closed his eyes and dreamt of spending forever just like this.

**Notes for the Chapter:**

> Ta-da, there you have it, a happy ending. I know some of you were expecting Cas to team up with the police to take Meg down and that's where I thought this was going too but then Crowley popped up out of nowhere and decided to save the day.
> 
> And that's the end of the story (or one of them anyway I suppose). I hope you enjoyed it; I may add things to this little universe from time to time if an idea or two occurs to me but if there is something specific you'd like to see, leave a comment or send me a quick message on tumblr (blue-reveries.tumblr.com) and I'll do my best to get you what you want.  
> Thanks for reading :)


	7. Ending B

**Notes for the Chapter:**

> Hello, if you haven't read chapter 5, you might want to back track and take a look, just so you have an idea of what madness I'm up to here.

The first thing Dean registered when he regained consciousness was that he was laying on a cold hard surface that bit into the side of him that was currently in contact with it. The second was that his shoes were gone and his hands were tied tightly in front of him with a zip tie.

Through the haze of pain in his head, he tried to put the pieces together.

Taking Cas to the bookstore and then blowing him in the alley.  
Dropping Cas off at the mansion and filling the car up with gas.  
Picking Meg up for her meeting.  
The change in the meeting’s venue.  
Dropping Meg off at the office building.  
Meg forgetting her bag and ordering him to bring it to her.  
Meg telling him she knew.

Oh god, she knew.

Despite his wish to act brave, Dean began to shake. He took in his surroundings; he must be in some sort of parking garage but there were only two black sedans, no other cars.

“Oh goodie, you’re awake,” Meg’s voice echoed from somewhere behind him followed by the sound of heels on the ground. “I wouldn’t want you to sleep through this next part.”

That was all the warning he had before a heavily booted foot kicked him square in the stomach, knocking every breath of air out of him; this was swiftly followed by another boot kicking him in the back, resulting in a sharp pain in his kidney. After these initial hits, he was unable to keep count and stock of where they hit him, there were just too many blows, though he was very much aware when they stepped brutally on his arm and leg. He heard the crack of bone and felt the sharp pain of bone breaking.

How long this went on for, Dean had no idea. They were careful to pull back when he was on the verge of blacking out though. In the one corner of his pain-addled mind, Dean deduced that Meg must want him awake for whatever she had planned for him.

He supposed it just wouldn’t do for him to be knocked out for his own torture.

One of the thugs of the two present who had just been beating him, forced him onto his knees. Dean hissed as this put pressure on his broken leg and the myriad of bruises on his body. His whole body throbbed in agony.

Meg walked into his line of vision, a satisfied smirk on her face. She held a pistol in her hand.

Well, he supposed this was it. The end of the line, at least the pain would stop.

“Go on,” he whispered hoarsely, spitting blood onto the concrete. Dean looked up into those calculating eyes, not feeling any fear. He knew this was always an option when he’d started seeing Cas, and over time he’d come to realize that being with the other man was worth it. Getting to spend time with a good person such a Cas and to be able to brighten the other man’s bleak life, even for a small while, was a worth this. “Do it, kill me already.”

A look of surprise washed over the woman’s face, she smiled horribly and threw her head back in laughter; a horrible pit began to form in Dean’s stomach.

“Kill you?” Meg said vibrantly, walking over to lay a hand on his cheek. Dean flinched at the contact. “I’m not going to kill you.” A part of Dean relaxed unbidden at this but tensed again as Meg continued, “He is.”

She jerked his head painfully to the left and he finally saw who was standing in the shadows as they stepped into the light.

Cas.

The look of shocked horror or rage at Dean’s appearance that the chauffeur had expected wasn’t there, instead the other man’s face was blank, his eyes cold.

The pit in Dean’s stomach deepened. This couldn’t be happening.

“Come on Castiel, do what you have to do to regain my trust,” Meg ordered, holding the gun out to her husband.

A fantasy of Cas grabbing the gun and shooting his wife before killing the guards and untying him flashed through Dean’s mind but to his horror, the dark haired man took the pistol and walked over slowly to stand several paces in front of him.

Easy shooting distance.

“Please...Cas, please don’t do this” Dean begged, looking up into those blue eyes that usually looked at him with affection but now were cold and distant. The hard concrete of the parking garage bit into his knees and he could feel his left leg throb in tandem with his heartbeat. “Please let me go….” Here he paused and, blinking back a few tears, whispered his guarded secret so that only the man standing in front of him would hear, “I--I love you.”

At first there was no reaction from the dark haired man besides a tightening of the hand, a hand that just mere hours ago had caressed Dean’s face worshipfully, gripping the gun pointed at Dean’s forehead and it made the broken chauffeur’s heart ache. Maybe he had been wrong...

“Dean,” Cas said softly, the other man’s tone had lightened, as if he too were pleading. Suddenly Dean had a wave of hope waft over him and his muscles lost a bit of the tension they’d accumulated during the beating.

He would be okay. 

Cas wouldn’t hurt him, he loved him. Dean knew he did.

“You were a plaything, nothing more” Cas said coldly, his brows furrowing in an expression of determination. “Goodbye Dean.”

The sharp pain of his cut and scraped skin and the fiery ache of his broken leg and arm were forced into the background as Dean briefly felt the sickening feeling of the bottom of his stomach dropping out in shock.

No...that can’t be right, this is wrong….

He looked up at the face of his lover one last time, tears streaming down his face as his heart broke in two and had a split second to register the sight of tears in Cas’ eyes before the deafening roar of a gun at short range echoed in his ears and a painless darkness engulfed him.

 

Castiel, pistol held limply at his side, stared down at the beaten body of his lover.

His Dean, staring up at him with a look of hurt shock. Those bright emerald eyes that were dimmed in death.

His eyes burned with the urge to cry but he suppressed it and instead chose to focus on the rage he felt as slow clapping echoed in the emptiness of the concrete hell he was in. Each sound was like a physical blow to his stomach.

_Clap!_  
_Clap!_  
_Clap!_

“What a lovely performance, _Cas_. Five stars all around, especially for our sniveling whore,” Meg sneered. Her heels clicked sharply on the ground as she sashayed over to stand next to Dean’s body, looking down at him with a self satisfied smirk. “It’s a shame he had to die, he would have made a lovely actor; what with all that begging. ‘Please, Cas! Don’t kill me!’ Top notch, truly.”

She nudged Dean’s shoulder with a bright red stiletto and rolled her eyes. Castiel flinched slightly, forcing himself not to reach out and push her away but of course his wife noticed. 

Meg always noticed.

She grinned evilly.

“Oh and we mustn’t forget my favorite part,” Meg cooed, walking over to stand behind him. He could feel her body heat against his back as she leaned in close to whisper in his ear. The sensation of her lips against his flesh made him nauseous, “‘ _I--I love you Cas_ ,” she mimicked cruelly, forcing her voice into a choked sob before reverting back to her mocking tone. “I bet the little slut didn’t even think I’d hear that but I did and it made this experience so much better for me. I haven’t had this much fun in years, maybe I should let you fool around before pulling the rug out from under you more often.”

Castiel said nothing; he just gazed down, transfixed by Dean’s dead stare. 

_...Please..._

_...Love you…_

He was brought back to reality by a sharp command from Meg to one of the two bodyguards standing sentinel by the cars. She ordered the taller one to ‘get rid of this trash’ down at the pier then meet them at home. The mindless thug did as he was told, callously pulling Dean up by his arm and dragging his body to the trunk before carelessly tossing him inside.

The sound of Dean falling into the empty trunk made Castiel’s stomach lurch.

“Now that that little bit of business is done,” Meg continued, not really caring that her captive audience had nothing to say as she walked over to stand in front of Castiel. She planted herself firmly and grabbed his jaw harshly with her hand, sharp nails bit into the dark haired man’s cheeks as his wife forced him to meet her eyes.

They were full of a cold fury that matched the fire burning inside Castiel’s stomach.

“If you even have half a thought of doing something like this again Castiel, if you even look at another man, this will happen again,” Meg said quietly but with no lessening of the rage in her voice. “I will grab another dirty little brat from the streets and you will either have to do as you’re told and dispose of whatever pathetic sap you’ve chosen as your lover or I will have one of my men slice that urchin’s throat and be warned, next time, I might not be generous enough to let the brat go unharmed when you inevitability come to your senses. This time may be the exception since it was your first offence but I make no promises for a second occurrence, do I make myself clear?”

Castiel glared at her, wishing that the force of his gaze was enough to set the evil bitch on ablaze.

“I said...DO I MAKE MYSELF CLEAR!?” Meg’s shrill shriek pierced his ear drums causing him to flinch.

Breathing heavily, Castiel met her gaze evenly. “Yes, you’ve made yourself very clear,” he growled quietly, his hand tightening into a fist around the gun in his hand. There were still some rounds in the magazine. Meg’s face morphed from a mask of fury to a relaxed state of smug satisfaction that made bile rise in Castiel’s throat.

That disgusting expression made everything easier.

“Has the child been let go?” he asked, mentally preparing himself for what was going to happen.

Meg rolled her eyes and let go of his face, stepping back two paces. “The little shit was kicked out onto the street again as soon as Rocko heard you put down that little bitch over the phone, just as I promised,” Meg drawled, obviously done with the situation now that she’d gotten what she wanted.

That was all Castiel needed to hear.

The next few minutes seemed to move at hyper speed and in slow motion at the same time.

Castiel turned quickly to his right, raising the pistol and leveling it at the lone bodyguard’s chest. The hulking man made to reach for the holster on his shoulder but was too slow.

**BANG!**

A blotch of red appeared on the man’s chest. Castiel didn’t know his name, didn’t know if the man had someone who would care that he never came home but then, Castiel didn’t care anymore.

Meg turned at the sound, a look of confusion on her face; Castiel moved forward at the same time so that he could pull her to him tightly with the arm not holding the gun. She looked up at him, realization dawning; their faces were close enough to kiss, like something from the cover of a romance novel. Glaring in fury, her mouth opened viciously.

“What the fuck do you think--”

Castiel brought the muzzle of the gun up to the underside of her chin. He narrowed his eyes in hatred at the woman who took everything from him, at his loving wife of almost ten years.

Pulling the trigger was easy.

**BANG!**

 

Several hours later, Castiel finally sat down in a ratty armchair inside his newly acquired hotel room. He sighed and poured himself a more than generous shot of whiskey, going over the list of necessary actions he had needed to take to make sure nothing was missed.

After shooting his wife and her bodyguard, Castiel had mechanically cleaned his face of the blood that had spattered him due to being at such a close range before pocketing the gun and Meg’s phone and walking out of the parking garage. Once he had made it out onto the street, he had stolen a car and driven back to the house; there was a lot of work to be done.

Such as using his knowledge of Meg’s business to turn over all the information he could find on her and her business partners into the police. However his first order of business was to text the thug who’d been tasked with taking care of Dean, telling him as Meg that she’d changed her mind the pier; she wanted to make Castiel watch as she had one of the boys ‘prepare’ the body for disposal so he was to return to the house right away.

All Castiel had had to do was wait for the man to pull into the spacious garage and step out into firing range.

The next part had been a bit more difficult, making sure Dean was found so that even if he parents would never know why their son had come to such a brutal and undeserved end, at least they could find some peace in burying him properly. Castiel had shot his lover in the chest despite Meg’s order for a headshot, refusing to force Dean’s parents to see that.

They would suffer enough as it was so he lovingly laid Dean in the back of the limo and drove him to the bad side of town. There he gently arranged Dean in the driver’s seat, took his lover’s wallet and made it look like someone had been rifling through his pockets before walking way and leaving the car.

A robbery gone wrong. Something the police wouldn’t bother to question in this rough neighborhood.

After this most important task was done, the dark haired man made quick work of walking to and breaking into Meg’s office and computer. All these years, his wife had thought he knew nothing about her affairs but in reality Castiel knew a lot; he was the son of a criminal after all. Uploading them to a public site for someone to find was also easy. Transferring money from the multitude of accounts that Meg possessed was a bit trickier but doable, and soon several charities had received massive anonymous donations and a hidden bank account was established for himself. This last action was more out of an ingrained habit to survive of course. 

Castiel didn’t plan on needing much money. Just enough for a quiet hotel room on the other side of town.

 

The gun felt oddly light in his hands, maybe because there was only one round in it now or maybe because of the sense of peace he felt knowing what that one round would bring.

Castiel took another slug straight out of the bottle of whiskey on the table next to him before leaning forward. His hands clasped tightly between his knees as a multitude of images flashed through his mind.

A flustered Dean watching him strip through the rearview mirror. He’d been so flustered, it had almost been adorable.

His eyes began to burn again.

Dean, gorgeous and desperate, writhing in his lap that first time together. Castiel had never seen anything more beautiful before that moment; nothing had been more alluring than that sight and probably never would be.

Tears gathered, blurring his view of the bland carpet under his feet; this made it easier to get lost in his memory.

Napping Dean, sleeping in the car on the way to the art festival, his face relaxed and peaceful.

Dean sprawled out beneath him in the car, his face now contorted in pleasure as they moved together, then the two of them laughing afterward. 

He was openly crying now, his face covered in trails of tears. His throat tightened painfully with sobs that were clawing to escape but he just couldn’t.

Dean, broken and beaten, looking up at him with pleading eyes; his cheeks wet with tears and smeared with blood.

Castiel blindly reached beside him, grabbing the gun on the table.

_Please Cas...don’t…_

Green eyes full of pain but with a flicker of hope, hope that is brutally extinguished by Castiel’s own cruel words mere seconds before they were darkened forever.

Cool gunmetal touched his shaking lips as his fingers worked to cock the pistol. The sound it made was deafening in the quiet room. He inhaled a strangely calming breath, finally ready to end it when another memory came to him.

_I love you..._

His eyes snapped open and he hurriedly took the gun out of his mouth and dropped it as if he had been burned. 

No, this wasn’t the way. 

After what he’s done, dragging Dean into his twisted life, not being a sane person and putting a stop to the two of them when they had the chance which ultimately led to Dean’s death by his own hand, Castiel didn’t deserve the peace that death would bring.

He had been selfish and that had lead to a bright beautiful soul being destroyed; living with the gut rending guilt would one part of his attempt to atone. Though he’d more than likely burn in hell anyway.

It was more than he deserved.

Castiel stood and walked over to his bag. He picked it up and was headed to the door when the gun caught his eye; it caused him to pause. The cowardly part of him pleaded for him to pick it up and put them out of their misery, the dull yet sharp ache in his chest joined in but he gathered his determination and turned away, leaving pistol lying on the floor.

A lifetime of heartache seemed a fitting punishment for killing the only person he’d ever love.

**Notes for the Chapter:**

> And there you have it, Ending B. I'm not ashamed to say that I was a bit choked up when I wrote Dean's death and how Cas dealt with the aftermath. I've never really written anything so sad before and I'm not entirely sure where this ending came from but it's been knocking around my head for a while now. I actually wrote this out first and then did Ending A so I could right something happy to counteract the sad feels.  
> To those of you who read this, I hope it lived up to your expectations and if you're like I was after writing this, I suggest you pop on back a chapter and cheer up with Ending A.
> 
> So here ends the story, if you have a timestamp or scene you'd like to see, leave a comment or shoot me a message on tumblr (blue-reveries.tumblr.com) and I'll do my very best to deliver since I love getting requests. As always, thanks for reading.

**Author's Note:**

> I wrote this as a non fanfiction-y drabble a couple weeks ago just to stretch my smut writing muscles and I just noticed today that, with a few simple adjustments, this was basically Destiel (go figure, haha) and since writing the next chapter of Awkward to the nth Degree seems to be slow going, I thought I might as well tweak the original story and make it about Dean and Cas. So hopefully you enjoyed my procrastination attempt :)


End file.
